DVC, but last-minute bookings only?

I've been to a few DVC presentation over the years and have been researching the resale market for the last year. Our situation is pretty unique, so I haven't been able to find anecdotes to compare with--was wondering if this amazing community can help shed light on whether our thinking is practical. For some context, we are an airline pilot family of 2 (significant other and myself, so travel is free), no kids, so studios only and we avoid all the busy seasons, but we do enjoy going the week after thanksgiving/early Dec. Our schedules are super flexible but are also never built that far in advance so we always book max. 2months out (usually closer to 1month or even just a few weeks out)-- we never stay for more than 2-3 nights, and we almost always go during the weekday.

(1) Resort location: given that we always book pretty close-in, we're most likely not going to be utilizing the 11mo home resort advantage at all, so my thinking is to book at the lowest cost/pt resort such as OKW or SSR since we'll be flexing our plans according to the availability calendars any way.

(2) Use year: we also want to prioritize being able to go the week after thanksgiving, or whenever the Christmas holiday decor is up, so we're thinking Oct/Nov use year. Is this how we should bee approaching this decision?

(3) We're looking at buying smaller resale contracts in the 50-100pt range to try it out and see if this works out for us, are smaller contracts easier/harder to re-sell if turns out this isn't a good fit?

(4) Given Disney's increasing disdain for resale and renting out points, do you guys see them putting further restrictions on resale members within the original 14 to only being able to use/rent points at the home resort down the line? I'm aware nothing is for certain, but is that within the realm of possibility? Because otherwise we would buy at our favorite resort which is AKL.

(5) Are there any tax deduction benefits since this is considered a property? I've seen contradicting info on this, was wondering if anyone has had any success doing so.

Anything else you guys can think of that we may be missing here? Appreciate your insights!!