Approach for Add-On?

So if I'm just going to spend points at VDH and I've got in the door with my initial Direct purchase, can't I just load up on cheap points elsewhere?
You won’t be able to use any resale points at VDH. If that is where you want to stay, it would probably be best to purchase what you need direct at VDH. I’d do a 150 point purchase to get the best incentives there and have them split into 100/50 point contracts.
 
If I don't have a hard preference for WDW resort, does the 7-month window still put me at a big disadvantage trying to book anything at all? It is probably blasphemous to some here, but we kind of don't care which DVC resort we'd stay at for WDW - we don't expect to visit often. Peak seasons notwithstanding, by the time you get to the 7-month window, is availability usually constrained across the board?

Really depends on what you are looking for and for how long. There are definitely times when getting a full week in a studio at 7 months in one place might be tough.

When would you travel? Would you be okay with a split stay? Or how about a 1 bedroom which are easier at 7 months.

And, they can change the booking window for non home resorts so while it’s 7 months right now, nothing prevents them from making that shorter

For example, they could decide to make the rules for VB different than other places. I just think if the goal is WDW with your resale points, then I just think it’s worth it to own the cheapest WDW resort vs offsite.
 
If I don't have a hard preference for WDW resort, does the 7-month window still put me at a big disadvantage trying to book anything at all? It is probably blasphemous to some here, but we kind of don't care which DVC resort we'd stay at for WDW - we don't expect to visit often. Peak seasons notwithstanding, by the time you get to the 7-month window, is availability usually constrained across the board?
If you don't have a preference, the ones that are most likely to be left remaining at any given time are Saratoga Springs are Old Key West. Definitely make sure you're okay with staying there. They're both great resorts but not for everyone. That being said, do I expect other resorts to be available at 7 months? Of course. There usually is pretty decent availability at 7 months if you're flexible with room types across the resorts but be prepared to stay at SSR/OKW if you can't find availability at other resorts.
 



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