I had a Mac 25 as my first sailboat. Decent boat and like you said not very overbuilt but probably good enough. I always envied the Rhodes.
The 25 can besailed with the pop top up. At least I could with my rigging configuration.
The trailer problem doesn't sound fun. You will probably end up finding another trailer for it in the end since its not made for the boat it isn't the best, by that I mean quickest too.
I could raise the mast and rig my 25 alone without a mast raising system but it wasn't the easiest. 30 min would be pushing it.
Id try to talk down the Rhodes owner.
Small is beautiful, simple, cheap, and easy......
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