I always am trying to come up with the next golf trip in the winter.
I think the key factors for choosing a destination are (in order):
1. Weather (as in days you can play)
2. Ease of travel
3. Food - needs to be adequate (whatever that means for your group)
4. Quality of courses (people will be more unhappy about bad food than bad courses)
5. Natural Beauty
6. Something interesting about the location
Cost - fits in there somewhere depending on your group.
My take on several destinations:
Southwest
Tucson - great weather - almost guaranteed to play, beautiful setting, varied prices
Phoenix - better weather, expensive
San Diego - wet this year, didn't get to play
San Antonio - decent courses, fun city, usually good weather
Amarillo - flat
Southeast
Fort Myers - private - Fiddlesticks is wonderful, public looks pretty sparse. Verandah is adequate.
Tampa - World Woods (great course - good prices)
Lake Oconee - weather is shaky before April, nice area, haven't played enough courses
Hilton Head/Charlston/Savannah - beautiful in April. Harbor Town is great fun. I would like to try more courses.
RTJ Trail - quirky courses, great prices, nothing to eat or do unless you are near a bigger city. Check the average rainfall amounts in deciding whether to go.
West
Denver - terrific climate, great number of courses
Monterrey - go there once
Pasatiempo - go there multiple times, especially in summer when it is firmer
Midwest
Des Moines - Low priced, The Harvester is worth the trip and play Wakonda (private - Langford),
Chicago - I've only played Cog Hill and really haven't wanted to play elsewhere.
Brainerd - some flights available. Play the Classic and fill with one or two other courses.
Duluth - Northland/Giant's Ridge, beautiful setting, warm for about 10 weeks
I really have enjoyed doing a combined sports event/golf trip.
A couple of years ago we combined seeing the local NBA team play in San Antonio with a golf trip. It added a nice diversion in the middle of the trip.
Perfect March trips include going to the 1st weekend of the NCAA tournament (I've done this in Tucson) or spring training baseball.