Regular visitors of Disney... do vacations every year sometimes twice.
Worth considering DVC. Compare the cost of DVC with other acceptable alternative options, whether they are comparable or not. Then see whether the price difference is worth the value (to you) of what you would get with DVC.
...family of 5, how long does it take to beat the price of financing & maintainance fees if you are accustomed to staying at the nicer hotels for under 200 per night.
You are used to a Disney deluxe hotel room at $200/night and this is an acceptable alternative (to you) vs. DVC. As your children grow, you may find the single bathroom less appealing. You also may find that you are unable to take vacations during school session. But for now, let's compare what you are able to do ($200/night) with what you could do with DVC.
With DVC, you must assume a 2BR is required for your family of 5.
...Sept...
You haven't mentioned your travel days... how may weekend nights (Fri/Sat nts) and how many weeknights (Sun-Thu nts) you are planning. So I'll assume it's a regular 7-night week in a 2BR.
Points required would be 218-270 depending on resort chosen.
Purchase price would be ~$16,000-$24,000 depending on home resort and source. Annual maint fees would be ~$800-$1,200. Consider a portion of your purchase price (10%?) and interest payments (if financing) plus your annual dues when looking at your total costs with DVC.
If you continued (at least for a few more years) as you have been, a week's accommodations would cost you ~$1,400. With DVC, it could cost you between $960-$3,000 for a week's accommodations. A lot depends on whether you buy at a resort with low maint fees and whether you buy a resale or get an exceptional incentive offer. It could easily cost you MORE to buy DVC than to continue as you are.
It's important to consider whether the probable increase in your costs is worth doing for you, for the added space, amenities and comfort of DVC.
...we might plan to use the points to stay at Poly or Contemp or even take a cruise.
Lost my DVC vote there. These options would end up costing you more! The cheapest rooms at Poly are 33 points weeknights and 60 points Fri/Sat nights, for 285 points/week. The cheapest at Contemp are 26 & 47, for 224 points/week. That's for a hotel room. Better off paying cash with no ongoing commitment, IMHO. Cruises are usually just as bad a value.
Does SSR have adjoining Studios.
"Adjoining" just means that two completely separate rooms are located next door to one another. "Connecting" means that occupants may move between two adjoing rooms by way of an interior door connecting those rooms, without exiting to the outside or common corridor. I am guessing you meant connecting. There are no connecting studio rooms at any DVC resort.
For connecting rooms, DVC only offers 2BR lockoffs - a 2BR made up of a studio connecting with a 1BR.
My kinderfolk are 9,5,4 & I hate buying two rooms because they still all crash on airbeds, cots, couches, etc.
There are a handful of dedicated studio rooms at BWV which have a very small, extra daybed, just large enough for either of your younger two children. However, in a couple of years, it would no longer fit and you would still end up needing a 2BR.
Do you need 6-12 mos. advance?
It's advisable. Adventure (cheapest) season is popular with folks who like to stretch points. Premier (Christmas/Easter) season is quickly booked as well. Other school breaks are next to fill up. If you are able to book more than 7 months ahead (preferably 11), then you will do the best. But if you are flexible, it may be possible to get later reservations. HTH!