Thanks again to all who've responded. I appreciate the feedback and am still saving. All the advice has cemented my decision for the WBRR.
1. Have you had trouble finding trees to hang on while camping?
Yes, but only in campgrounds where there is a designated tent "pad". The first time I camped in a campground, I got lucky and the trees were in the right place. I built myself a Turtle Dog stand, which took me all of about 30 minutes, in case I went car camping somewhere without trees. There are hammock stand backpacking devices make with lightweight materials but they are more expensive.
2. Is it hard to set up ?
Easy peasy. Easier than any of my tents.
3. Would you buy it again if?
Absolutely! I set it up for the first time in a park, laid down to try it out for 5 minutes, and woke up an hour later. Oddly, I found I didn't need a pillow.
4. Do you recommend it for a first hammock?
Definitely. It has all of the features I needed. I didn't find it to be unstable at all, which is a common concern.
I also got a SuperFly because I wanted the doors built in, rather than the Cloudburst, which has no doors. The CB has the pullout positioned differently than the SF. I bought 4 clip-on tarp pullouts from Dutch Gear so I can easily set the pullout position like the CB.
I tried 2 different gathered end hammocks and couldn't quite get past the calf pressure problem. I didn't really want a piece of equipment that required me to fiddle around a lot to make it comfortable.
Oddly, I found I didn't need a pillow.
“I held a moment in my hand, brilliant as a star, fragile as a flower, a tiny sliver of one hour. I dropped it carelessly, Ah! I didn't know, I held opportunity.” -Hazel Lee
I tried my Ridgerunner last night with my Exped Downmat pad. Firstly, wanted to see if it would fit as I have the 26" wide version. It fit fine and was snug at the waist of the RR so it is not going to move. This is a 3.5 inch thick mat and I had never tried one that thick before. The size and thickness of the mat fills the RR side to side and end to end and raises the bed up -- but I did not find it to be too tippy at all and the view was great! Plus, the pad has an R value of 8 (see link below) so an underquilt should not be necessary (in addtion to the pad) in just about any conditions.
When I tent camp, I use the pad plus the tent, poles, stakes and sleeping bag. With the RR it is the pad, plus the hammock (no stakes) and a TQ (and sometimes tarp). From a standpoint of packed size and weight, pretty even (I motorcycle camp).
Comfort? RR is awesome. I like it better than my BB.
I will say though, that the RR with the thick pad is a like a cot in the sky. It is quite different from a gathered end hammock. YMMV.
Other tips for Florida hammocking? DEET is your best friend and get a broad brim hat.
Watch DEET around hammocks and tarps. It will melt the fabric. Permethrin is a better friend for those.
Good point, as matter of fact, got a spray bottle from wally world last week. Permethrin for plastics and fabrics, DEET for the skin.