I started with 25 OKW resale in 2011 (because I wanted a member account in order to manage my own reservations, and that is what I could afford at the time as a single Mom of 3) and added 50 Poly direct when that opened (again, because I could afford that). 3 years ago, I sold the OKW (at a profit). I have gotten transfer points several times (usually when I wanted to stay somewhere else and have 11 month advantage). I've loved having the AP discount when that exists (have an unused Gold voucher hanging out still) and am grandfathered in on blue card. This works for me because I can sometimes do 5-11 months reservations, but I often end up being more last minute than that (when I wouldn't be able to use my points anyway because nothing is available), so I'm not left stewing over unused points. I would suggest really looking at what you plan to do, sketch out what you think you'll enjoy and has the value you want to get out of it. I've thought several times about adding boardwalk points, but can't justify the cost with the 2042 expiration.