I'll start from the bottom: Hull core problems in the 25 are very rare. The cockpit deck may have some water intrusion around access hatches where screws penetrate the core, unless the core is epoxy sealed--and screws into epoxy plugs. This is easy to do on the 25 and can be all done in less than a weekend. The boats most susceptible to core problems, are those which are stored out in the open in freeze thaw cycle weather. For example, when my boat is not under full cover, I have a slant back over the cockpit--no water gets in the cockpit or bilge.
Dinghy: inflatable every day. I have a hard dinghy (9' Fatty Knees, Lyle Hess design). I would never think of putting it on the 25 (or any other C Dory)--even on my Cal 46, it was a problem. A RIB was much better. The only boat I had a hard dinghy on was one where I had permeant davits to lift the dinghy.
Air floor inflatable is best. My current dinghy is over 20 years old. Still looks almost like new. I keep it stored, rolled up in its container, wash after every trip and treat with AeroSpace 303 each season
Davit: Garhauer crane davit--more robust than St. Croix, you can get it a foot or 18: or even 2' longer if you want. Ours is 12", probably if ordering again I would go 18". It will lift 150# (actually considerably more). Excellent blocks with 6:1 purchase. Get the larger of the two models. See my phots for mounting.
You could make a mounting which would put the dinghy over the AC unit or even flip the dinghy upside down over the AC. But could not use the AC then.
Another option is the cantilever Bimini. See Sea Otter's album. Blue Coral here in Pensacola made the first ones. Sea Otter's owner, Tom, has a place near Ocala, FL. which makes them. They could be strong enough for a light inflatable--perobably put a radar arch, and that support part of the dinghy weight and the rest on the cantilever top.
I do like the 9200 Coleman RV AC unit. It will run off the Honda 2200 with no modification... But I would put an ""Easy-Start" system on, so the generator could run on eco mode. The marine AC's take up a lot of room inside of the boat's cabinets and storage space. You can only run them when in the water; mud, sand, weeds and jelly fish plug up the strainers. The RV or window will run on the trailer (boater homing in RV parks) or when the boat is on a lift. Gulf Coast John, will tell you to get a 15,000 AC...
In our boat we use the $129 "Arctic King" from Wal Mart--5,000 BTU, will run on a Honda EU 1000. We have a block and tackle plus a mount system that makes it easy to bring up from under the V berth to the opening front window. Most of the time this is used at night for sleeping. It brings the temp down 20* below ambient. So it 100 outside, 80* inside. We also have fans to circulate the air. Although we have run at low speeds with the window AC in place, I don't recommend it.
It is rare that we run with air conditioning--even when we had the roof air. Windows open and there is a good breeze, in the summer in Pensacola.
My preference is a fiberglass interior. There is slightly more room in the cabin, there is slightly better storage. The argument is that wood is more easily modified. Having worked with Fiberglass and wood for over 60 years, I would say that fiberglass is easy to work also. The newer boats have the SeaLand Traveler type of commode: fresh water flush, 9 1/2 gallon holding tank under the toilet. It is a much simpler system and more reliable than the older boats which have a 20 gallon holding tank and macerator pump all of the way aft. Lots of tubing. I had the macerator pump go out in AK, where there are few pump out stations on my first 25. (2003 model). Our current boat has an "Air Head" composting toilet--some advantages and disadvantages, but we now consider it the "best solution"...
Go thru the albums of 25's You can find the 25's by going to "our C Dorys' and sort by model #
If you have specific questions, please PM me--I can give phone # or e-mail for more details. If we didn't have all of this CV19, I would say come on down for a few days and check out a couple of 25's here in Pcola.
Welcome aboard!