I usually choose the mid-tier as the average Westin, Marriott, etc., where I'm redeeming points is actually a resort and at the top of the chain's quality list. Marriott Wailea, Marriott Aruba, etc., are all plenty nice.
I hotel hop when there are very lucrative per-stay bonuses, and at the beginning of the year to get the SPG 25-stay PLT done for the year (already done for this year, in 27 nights). It's a bit tiring, so I'm now at normal 3-4 night Marriott stays, not trying for that extra 500/night.
Just make 5 reservations in the same hotel.
You can check out leave with the concierge and recheck in in the evening.
Choose different types of rooms.
Most programs will recognize this as one stay, which it is by the rules of the program.