We have 1660 points and another 150 we are waiting to load. DVC is a huge part of our retirement plans. We live in PA, so avoiding as much of the winter as possible is the plan, and we did not want to deal with the hassles of owning and maintaining a second home. We typically head to HHI for the week of Thanksgiving and then head down to Copper Creek for between 1 - 2 weeks. Then we head back down in Jan / Feb splitting time between HHI and WDW (adding VB for the first time soon) for about a month. We mostly drive so don't have to worry about flight costs. We'd stay longer but my husband has to have a medical treatment every 4 - 5 weeks so we have to make the trip back to PA. Which honestly, I like. USPS only holds mail for 30 days at a time and it's reassuring to come back and check up on things, see our son, etc.
We usually add in some shorter fall or spring trips as well. We avoid summer like the plague. Our son and his fiancee sometimes join us for a short time as their vacation days allow. They also occasionally use our points on their own. We are all heading to Aulani this fall. Our son is listed as an owner on all of our contracts, so once we are too decrepit to use the points they can decide which contracts they want to keep and we'll sell the rest.
We mostly stick to resorts with favorable
point charts. That was a big consideration in choosing our home resorts - CCV, HHI, and BWV. Thankfully those are our favorites so it all works out. We'll occasionally splurge on a more pricey resort, but only for a few days to save points. We almost always book a one or two bedroom, so a nice
point chart is essential for us. We are not studio folks.
We have not regretted a single penny we've spent on DVC. We purchased our first 500 points (over 3 different contracts) direct from Disney. All of the rest are resale. We like our mix as we have plenty of points to occasionally stay at any of the restricted resorts, but buying so many through resale allowed us to afford so many more points. We have never rented any points. We had a rough couple of years where we couldn't travel much due to my husband's health but between banking and our son, managed to not leave any points on the table. He got the ok to travel last October and we've been happily blowing through our backlog ever since

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