Having visited the Maldives and Thailand on one trip myself because of easy logistics,

1) stay at a resort with boat access. Don’t waste time on an airplane. Check out como for good value.

2) skip a second beach resort in Thailand. For some contrast, and something we did, fs gt or anatara to save some $.

3) 4, 3, 3 Maldives, Bangkok and up north could work.

4) don’t worry about points or free buffets too much. If it were me in your shoes, I’d say como, some place in bkk for free on points and fs gt (or Ana) m. Doable but delete Samui imo.

Fs Chiang Mai, meh to me. I didn’t care for the hotel at all during our stay

congrats