Additional Points:
Do get the heavier capacity trailer. I put three spare tire mounts on mine. If you have a serious flat that can't be repaired (common with radial tires) you won't be able to easily find a replacement on the road; e.g., Sears does not sell trailer tires at all. These are serious 8- (or in my case 10-) ply tires and if you are lucky enough to find a replacement it may cost your towards $300. Driving for days until you locate a new tire without a spare is scary. Get bunks and pay a little extra to have "cutouts" installed so sling straps will easily fit under the boat to remove it from the trailer. You may never have to put the trailer in salt water if you use it twice a year for storage. I'm not nuts about my factory provided EZ Loader trailer, although you can get parts anywhere. The Float On models look better. Denny-o's advice on the Loadmaster is probably good advice.
Definitely replace your anchor lite with an LED bulb. I also replaced the bulbs in the head and cave with LEDs as they are often on; we leave the cave light on as a night light to get to the head. Someone else on this site pointed out that whenever the running lights are on, then the engine is on so I did not bother replacing them with LEDs and there is a question as to whether they are Coast Guard approved... I use a little battery powered camper lantern in the cabin and, thus, see little need to replace all the cabin lights with LEDs, the red chart lights already are LEDs I think. Most of the time in the cabin you'll be reading your iPad/Nook, watching TV, writing your blog on the computer, etc. and thus have little need except while cooking for overhead lights.
If you want to head further south, reconsider getting the diesel (expensive) generator AND factory AC, if you will be on the hook in Florida. If you stay in marinas, then the Honda is the way to go. Also, on the hook having the solar panel(s) can keep your refrigerator alive without having to run the engine/generator a couple hours per day. You can buy the exact same solar hook-up aftermarket if you want to save a bit up front on a new boat purchase.
For MD and further south, you would not need heat on a regular basis like our sister ships who motor all winter in the Northwest. Save around $4000 on the Wallas in that case and go with a $60 Mr. Heater Little Buddy (
http://www.northerntool.com/shop/to...3668&ci_sku=173668&ci_gpa=pla&ci_kw={keyword}). Use a little butane stove from West Marine for cooking, as opposed to the electric range top.
An autopilot is wonderful, but since you are considering a R25sc you could save $5000 by aftermarket installing a Raymarine S1000 for under $1000
([url=http://www.thegpsstore.com/Ra...w.thegpsstore.com/Raymarine-Sm ... 4AodBFaLmQ)[/url]. I can't imagine a Ranger without the wonder binimi system. Mine has both screen and plastic window panels sets. Again you can save a bit by buying this stuff aftermarket and installing it yourself or with a local canvas maker by buying it from King Marine who has the templates as they make this stuff for Ranger.
A great thing about a new boat is you can install an AirHead composting toilet like Denny-o suggests and that I have. With a new boat, convert what was the holding tank to spare fresh water tankage and shower as much as you want while in the wilderness.
I kept the cave, my buddies seem OK sleeping there. I bought a set el-cheapo plastic drawers (like a small bureau) and move it from the cave to the V-berth when friends (actually one friend is all that would fit) use the cave. Of course, the cave is really useable on a R25, I don't care for the flip up seat system on the R25sc. Also, since you don't need to flip up an R25's seat and have easy, constant access to the cave with a chart table above, you can mount a toaster oven and spare stuff above the save in a R25. More about that a little later...
Skip the anchor package and install your own stuff after study on this bulletin board. It will likely cost you a bit more, but you can have a better and heavier rig (in my case a Rocna). Maybe money isn't an issue for you(?). For me, in order to rationalize a new boat I had to save where I could with the plan to add stuff gradually, using equipment equal to or superior than the Ranger Standard stuff (except for the Raymarine autopilot).
Another consideration (which has been debated in other threads on this bulletin board) is whether you might prefer a R25 with a bigger cabin vs. the sport cabin you are probably looking at. I'd love the have better access to the front end of my engine, but we spend a lot of time in our cabin and I would not trade that interior space (R25) for the increased deck space (R25sc) and you lose a couple of port holes and lots of other stuff. In fact the R25 cost $10,000 more base than the new R25sc. You seem to have ruled out the R27 so I suspect you are sensitive to cost issues. A very nice option would be a used R25. I believe Ed and Elaine Henn's fabulous R25 is still for sale near you at Chesapeake Ranger Tugs:
http://www.chesranger.com/. BTW, get a blue one.