Give it to me straight...

If you are in the market at the 300 point range, I would buy 2 contracts. One OKW direct with minimum direct points needed for benefits (is it 100 points?) and the second resale. I would not buy resale OKW because the contract length is too short. As others have pointed out, if you buy OKW direct, you automatically get the extended contract. You can put the entire direct purchase on a credit card.

I would not buy at Vero unless you want the Vero booking advantage at 11 months. Vero member fees are HIGH. Once you are a member, one of your main concerns will be MF. And with Vero you have hurricane risk and that could cause even higher fees. If you do not book early and would not benefit from the booking advantage, I would buy at SSR for the resale contract. Low MF and it has enough years left on the contract to resell if you decide to. Even though we are about 5 years older than you, I wouldn’t buy the really short contracts unless you are, for example, a Boardwalk diehard who will book at 11 months every time. Having the option to resell is very comforting. I think with the shorter contracts you will have much less flexibility to do this in the near future. There are other good resale locations besides SSR, although if you enjoy food, SSR is a great location for dining options at DS. I would just look at price per point, member fees, and length of contract. Good luck:tink:
 
I am looking at resale contracts and noticed Vero is significantly less. So, I could make that my home resort and still book at OKW at seven months? Is the only advantage to buying where you want to stay Is so you can book at 11 months? We’d probably rarely stay at Vero but since the cost of points are significantly less if we could get a Vero contract and book at OKW Then we’d be happy campers. Or are there restrictions if you buy into Vero thru resale?
Watch out for the maintenance fees at Vero (and Aulani and Hilton Head). They're significantly higher than the WDW resorts and would likely end up costing more over the life of the contract than the amount you save on the initial buy in.
 
Thank you all for the good advice. I think we are leaning to going direct to buy OKW for 100 points, just to have the perks and since OKW is our favorite resort, would have the longer extension thru Disney. We wouldn't finance just pay it in full.

Then look for a good SSR resale for 100-150 points.

When I called Disney to get an idea of cost, it's 165 a point for OKW with 100 pt min. There is a $750 discount if you purchase 150 pts. The rep was encouraging me to do a Feb use year as I will then get the Feb 2020 points but not have to pay the full annual dues for 2020, just a prorated amount... I was getting confused on that piece, so does that mean if I wanted an August use year then I wouldn't get the 2020 points and/or have to pay a full year of 2020 annual dues? Trying to understand... If we prefer to go in Sept/early Dec/Jan and sometimes Feb... is the best use year for us August?
 
If you get the Disney Visa, you can get 6 months interest free. You could put your direct purchase on the Disney Visa, pay it down as much as possible in the 6 months, and then transfer the remaining balance to another interest free credit card for 18 months. You will have to pay a balance transfer fee, and this assumes you have excellent credit and can qualify for a high dollar limit credit card. But that 3% fee is a heck of a lot less than paying monthly interest over several years. Plus you get 2% of the purchase price back as money you can spend at Disney when you charge it to the Disney Visa. Just a thought to give you some flexibility in financing. I would only do this if you are very disciplined in paying credit card balances off in time.
 

Thank you all for the good advice. I think we are leaning to going direct to buy OKW for 100 points, just to have the perks and since OKW is our favorite resort, would have the longer extension thru Disney. We wouldn't finance just pay it in full.

Then look for a good SSR resale for 100-150 points.

When I called Disney to get an idea of cost, it's 165 a point for OKW with 100 pt min. There is a $750 discount if you purchase 150 pts. The rep was encouraging me to do a Feb use year as I will then get the Feb 2020 points but not have to pay the full annual dues for 2020, just a prorated amount... I was getting confused on that piece, so does that mean if I wanted an August use year then I wouldn't get the 2020 points and/or have to pay a full year of 2020 annual dues? Trying to understand... If we prefer to go in Sept/early Dec/Jan and sometimes Feb... is the best use year for us August?
A February UY would be a very poor choice. Your travel plans are for the last 5 months of that UY. The banking deadline for Feb UYs is Sept. 30.

If you were to choose an August UY, you would get the 2020 points. If you choose a Sept UY, you would get the 2019 points ( because August 24, 2020 falls in the Sept. 2019 UY) plus the 2020 points on Sept. 1 provided the purchase goes thru before the end of this month and the guide banks your 2019 points as a courtesy.

When it comes to paying the dues, it can get fuzzy. Dues are paid in January of every calendar year, regardless of your UY. When you make a direct purchase from Disney, they prorate that years’s dues based on the number of days remaining in the calendar year, not how many remain in your UY. So regardless of whether you were to choose an August or February UY, the amount that you owe for 2020 dues would be calculated based on the number of days remaining in 2020.
 
If you told the rep that you liked to travel in December and January and he tried to sell you on Feb UY, I don’t think he has your best interests in mind. Any UY will give you 2020 points, and those that come after August will give you 2019 points without the maintenance fees For 2019. That is, if you buy in August. Plus, you would be able to bank them, so you will be starting out with twice as many points.
 
Thank you all for the good advice. I think we are leaning to going direct to buy OKW for 100 points, just to have the perks and since OKW is our favorite resort, would have the longer extension thru Disney. We wouldn't finance just pay it in full.

Then look for a good SSR resale for 100-150 points.

When I called Disney to get an idea of cost, it's 165 a point for OKW with 100 pt min. There is a $750 discount if you purchase 150 pts. The rep was encouraging me to do a Feb use year as I will then get the Feb 2020 points but not have to pay the full annual dues for 2020, just a prorated amount... I was getting confused on that piece, so does that mean if I wanted an August use year then I wouldn't get the 2020 points and/or have to pay a full year of 2020 annual dues? Trying to understand... If we prefer to go in Sept/early Dec/Jan and sometimes Feb... is the best use year for us August?
A Sept UY would give you the most points and at the cheapest amount total when looked at for total points assuming you get the 2019 points. Retail you can bank until the last day of the UY. But I would get the best UY as I think it's more important than the small amount of savings and few months of extra points for many if not most people.
 
September is perfect for you-push for that! February would be the worst possible for your pattern of travel-it bothers me they tried to sell that to you.
 
And as far as Maintenance fees,the dues are prorated from the month you buy, not from your UY. I think that’s correct, you pay dues from September on.
 
We have August use year. We really did not know what to pick because we go at different times. We ended up picking a resale contract that we liked and that determined our use year. We went back and bought a small direct contract a year later for the AP discount and Epcot lounge (lol) benefits. We travel to wdw in September and November, but we also travel in June and August. Not every year. Last year on a whim we went in February and had a trip booked for Memorial Day in May. All over the map, so it would be hard for us to pick the “perfect” use year. If we had cancelled the May trip, we would have been in a pickle (to put it politely) to use those points before July 31. As it turned out the trip got cancelled by Disney (and COVID). With an August use year, we were at their mercy. We had not really fretted over UY until this instance. If you are sure when you will travel, I would pick your use year to begin the month before you travel. It gives you the most flexibility. I think the guide was just saying that you would not have to pay dues this year if you go with February. In a way he is right, but that would be a very bad use year to pick if you travel in September and December. 8-)
 
When I called Disney to get an idea of cost, it's 165 a point for OKW with 100 pt min. There is a $750 discount if you purchase 150 pts. The rep was encouraging me to do a Feb use year as I will then get the Feb 2020 points but not have to pay the full annual dues for 2020, just a prorated amount... I was getting confused on that piece, so does that mean if I wanted an August use year then I wouldn't get the 2020 points and/or have to pay a full year of 2020 annual dues? Trying to understand... If we prefer to go in Sept/early Dec/Jan and sometimes Feb... is the best use year for us August?

The whole thing that the guide told you about "prorated amount of dues" doesn't make any sense. You'd be paying the full dues on the amount of points that you buy. Also, as others have said a February use year makes zero sense for you. August would be a much better use year for you.
 
UY....I taught and always had spring break in March, and March was perfect. Well, we retired and like wereofftoneverland we travel during all months and hope for the best.
 
The whole thing that the guide told you about "prorated amount of dues" doesn't make any sense. You'd be paying the full dues on the amount of points that you buy. Also, as others have said a February use year makes zero sense for you. August would be a much better use year for you.
They prorate buying retail based on the number of months remaining in the calendar year then you pay the dues again for the next year due in Jan. So you do pay slightly less if you buy retail later in the year. But it's based on the timing of the points and when you buy, not the UY itself. Now if you bought a Dec UY and didn't get 2019 points (which is the current UY for Dec) you'd pay 1 month only (Dec). You'd pay exactly the same prorated amount if you buy now and get the current points for any and every UY. However, if you bought Sept now, you'd get the most total points because you'd get all of 2019 AND in a week, another allotment for 2020 UY.
 
They prorate buying retail based on the number of months remaining in the calendar year then you pay the dues again for the next year due in Jan. So you do pay slightly less if you buy retail later in the year. But it's based on the timing of the points and when you buy, not the UY itself. Now if you bought a Dec UY and didn't get 2019 points (which is the current UY for Dec) you'd pay 1 month only (Dec). You'd pay exactly the same prorated amount if you buy now and get the current points for any and every UY. However, if you bought Sept now, you'd get the most total points because you'd get all of 2019 AND in a week, another allotment for 2020 UY.
I understand what you're saying, So that would only be the case if OP closed after their use year started, correct?
 
They prorate buying retail based on the number of months remaining in the calendar year then you pay the dues again for the next year due in Jan. So you do pay slightly less if you buy retail later in the year. But it's based on the timing of the points and when you buy, not the UY itself. Now if you bought a Dec UY and didn't get 2019 points (which is the current UY for Dec) you'd pay 1 month only (Dec). You'd pay exactly the same prorated amount if you buy now and get the current points for any and every UY. However, if you bought Sept now, you'd get the most total points because you'd get all of 2019 AND in a week, another allotment for 2020 UY.
Yes, when we bought ours in May, we only had to pay prorated dues but got the full years allotment of points.
 
I understand what you're saying, So that would only be the case if OP closed after their use year started, correct?
NO, it's the case for any purchase if you get current points no matter the UY. Fees start from the date you sign the forms or the date you get points if they're delayed such as the no points until Dec example I gave above.
 
I am looking at resale contracts and noticed Vero is significantly less. So, I could make that my home resort and still book at OKW at seven months? Is the only advantage to buying where you want to stay Is so you can book at 11 months? We’d probably rarely stay at Vero but since the cost of points are significantly less if we could get a Vero contract and book at OKW Then we’d be happy campers. Or are there restrictions if you buy into Vero thru resale?
Buy VB or HHI if that is where you want to stay most of the time. Buy a WDW resort if you plan to use your points at WDW most of the time. If DLR is your main resort, buy your points there. You need the 11 month booking for Dec, even at OKW.
 















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