My situation now is that I'm retiring next year and financially, I can afford to buy what I want. The surprising thing is that I want a MacGregor 26D.

The boat I'm a whisker away from purchasing is in reasonable shape for a 35-year-old boat. The original trailer is in pretty bad shape, which is no surprise. I would already have the Mac in my driveway if it wasn't for the trailer, that I was afraid to pull down the road. When I was younger, I would probably have hooked it up and pulled it home. Whether it is wisdom or excessive caution, depends upon where you stand.
I've read and searched through these forums and it is surprising to me that there isn't an easy guide to modifying a standard trailer to fit the Mac. From looking at the dimensions of the trailer, it doesn't look all that difficult to make any >20ft trailer work for someone willing to modify the bunks and the axle position to dial-in the tongue weight. I know there is a new one available via Super Sport Marine. I talked with them and they seem like great people but I'd have much more invested in the trailer than I do in the boat. I'm inclined to buy used galvanized trailer and modify it to make it work which I think can be done for less than half the price of a new one. Any wisdom anyone has on the trailer modification, I'm all ears.
The other issues are on the boat itself. The hull itself looks warped on the aft section above the water line. I've read where people think that the stock Mac trailer warped the hull over time just by sitting on the stock trailer. As long as it doesn't impact the performance of the boat, I'm 'ok' with that. Most people wouldn't notice.
The second boat issue is that the non-slip on the deck is damaged where the mast supports enter the deck. Not on the chainplates, but on the little stays that stabilize the mast as you raise it. It appears that someone lost control of the mast while raising it and pulled the stabilizing support enough to damage the deck. I tapped around it to check for deck rot and other than right near the stress crack, the deck appears solid. Either way, I'm going to need to cut it out, and glass it to repair. If anyone has done this repair, I'd be interested in your input.
Anyway...I'm looking forward to being a new Mac owner! Working on the boat will be part of the fun.