I am not fond of surge brakes for just that reason, I went with electric. Like any brakes, they need maintenance, but they work well (although drum brakes probably aren't so good in salt or brackish water).
No power at his lift.
Even with the water warming the hull, I don't think I'd leave it unless there was a heat source for the engine bay. I'd be draining it, if it were my boat.
I used a similar product on my deck - Durabak. A bedliner-like rubberized coating. The stuff is horrible. Not durable and where it hasn’t peeled or worn thru, it will be a huge pain in the a$$ to remove. Never again.
The OEM switch also has nice bullet connectors that tap right into the harness. No slicing of wires required. It also looks very nice and does not protrude much at all.
Just be sure to put the gear selector in Forward before pulling the drive. Not that any of us here have forgotten to do that before tugging on the outdrive... 😬
I'm not sure about the other bits, but I've heard of quite a few problems with aftermarket bellows. That job is such a pain that I could not imagine using anything but OEM parts. I'd have to have to re-do it in a year because some cheaper parts failed or didn't fit right.
My boat has bumpouts on the transom, but they're near the top on both sides. They are just fiberglass with expanding foam poured in; they would not be suitable for mounting swim platform brackets.
I'd be concerned yours are similarly constructed. I'd much rather anchor into a flat section, so...
This is an expensive time to buy a boat (both springtime and the COVID situation have prices inflated considerably). Used boats are going for a premium now, so book values may not mean much.
I would be much more concerned about structure issues for a boat that admittedly has been left outside...
Does that strip along the keel just behind the bow have wear all the way through the fiberglass? It almost looks like there are holes that you could stick your finger into.
If you plan to beach the boat, after fixing the keel, consider buying a KeelGuard or a KeelShield. We have a KeelShield (from Gator-Guards) on our boat, and not only has protected the keel quite nicely, it has held up really well over the years.
I'm pretty sure that's not an IL law, but a Barrington law... unfortunately, some communities and homeowner's associations are pretty restrictive. I'm glad I live in an Illinois community without similar laws. Is off-site storage an option? You probably could rent storage somewhere that would...
You mention you'll be using this in IL and WI waters... which ones? I think the kind of boat used on smaller lakes or rivers might be bit different than what you'd want on Lake Michigan.
It also would be useful to know how you'll use the boat (fishing, watersports, day cruises) and how many...
Buying a new boat and hoping you can retrofit a windshield (assuming that's important to you) sound like real pain to me. (And possible an expensive pain...)
Those look like fun boats for warm and mild weather. On even a slightly cooler day, riding out in the wind can get pretty chilly.
If you can figure out a way to do it cheaper than $2500-3000, more power tp you. But my experience and that of many others here suggests around $3K is typical.