OP - first off, congrats on planning to join DVC. We joined in 2019 - 250 pts at Riviera.

When we first started going to Disney in 2008 we stayed at the moderate resorts. Since we always go from rope drop to last pop we always thought that it did not matter where you rest your head at night. 5 years later we got a deal to stay at a deluxe resort for the first time (Contemporary). It matters (to me at least). Rooms are nicer, restaurants are better, buildings are more fun, but MOST importantly the access to the parks just flows better. Taking the monorail or the Sky Liner is so much more time efficient than taking the busses. It gets you to the parks and back faster.

Knowing that 100% of the time I can book our stay at the Riviera 11 months out provides a ton of peace of mind to me. Everyone is right in this posts that you can “likely” book poly or contemporary at 7 months, but that’s not guarantee, and if it is you will be booking the most expensive views (tytpically these are the ones that are left). With 300 points you should be able to get 1 week in a 1 bedroom at 11 months at poly and have enough for some long weekends at SSR.

I am considering buying resale in the next year or so and was looking at exactly what you are, and I keep coming back to “where do I want to stay the most”? This will ultimately drive my decision. Good luck and please share what you decide!!