Our CYV community is 9 years old this summer and has 80 villas. About 40 including mine have had them repainted the past year or so. The other 40 have not, but I would guess will have to have it done in a year or two. I went ahead and did mine because it needed it and I hated the original pale yellow and we were allowed to change to one of 20 colors. Essentially it was green, gray or 18 shades of brown. I chose the green because it was the most drastic difference. I would of like white, but that wasn't an option.
We used Oscar who power-washed the whole exterior, that really made a difference to the soffits and rain gutters, they looked like new. Then 3 days later 3 or 4 guys came and removed all the downspouts, sealed all the cracks, and rolled on two coats of Sherwin Williams best exterior paint.
Before taken in 2013
After, taken last October