Re: 14' 1958 Fleetform Restoration
Doesn't look like you are getting much help on your questions, so I'll throw in what I know, which may be too little. First off, we had that boat when I was a kid, and I have many fond memories of learning to ski and boat with it. Secondly, you are in a good position with that boat as it has minimal interior "junk" to work around, and no false floors. That will make your job much easier.
1. Why a new trailer? Is yours bad beyond repair? It looks a llittle wide, but that's no problem. As you won't be boating for a while, I'd save the money and not buy a new trailer now. The finished boat and motor will weigh less than 1000 pounds, and small boat trailers are a dime a dozen. The original trailer for our Fleetform is still on the family farm, and it is little more than a long tube with an axle and bracing with bunks. Don't overthink a trailer for this boat right now. Even new trailers will need annual maintainance.
2. Is the transom rotted? why do you want to replace it? Assuming it is bad, make sure you replace it with good marinegrade materials. As I'm new to this site, I don't know if there are detailed instructions on how to do this here, but if not, there is a site I frequent for Offshore powerboats Only where there have been a few transom replacements and the instructions on how it was done. Most of these boat have large sterndrive's, not outboards, but I'd think the process should be the same.
3. Hull repair. Is just the gel coat damaged, or is it more than that? Need to know what's wrong to comment further.
4. We had a body shop spary paint ours, and that would be the easist I'd think. If you do the prep work, the paint itself may cost more than the labor to spray it.
5. Sounds like you have a good idea of how you want it set up. The original did not have a back seat, and we kids sat on the rear floatation with the skis setting on the floor between us. (Dad was happy when we upgraded the motor to one with electric start, as he no longer had to walk on the skis to pull the cord). You might consider adding gauges to a pod that is clamped in place, rather than drilling holes in the dash, as the hole is forever, and is not original, if that is important to you.
6. See 4.
7. Isn't the bed liner heavy? Otherwise, sounds like a great idea. There are "non slips" that can be added to wet paint that might accomplish your goals.
9. I think Taylor makes a old fashioned buble windshield like many boats from the 50's used. Or, the junk yards is a good idea.
Good luck with your project.