A big thanks to everyone who has been contributing to this thread. I've read your advice and appreciate it all. I'd like to respond to each of you but time is short today.
I was able to see the boat last evening just after sunset. The initial looks from my inexperienced eye were good ones and I walked away excited. I woke up this morning more critical and grounded, enjoying the back-to-reality effect "sleeping on it" has had.
For various reasons (time, fear that I've already advertised this boat way too much on my own here and elsewhere, not wanting to bore, etc…) I'll not go into deailed specifics nor post all of the photos taken (there are many). For anyone who has taken an interest in this little quest or who is just curious to hear more or perhaps lend some more advice, PM me and I'll be glad to go over everything in detail as I'm wanting to do by the minute.
I liked the current owner / seller. Seemed as genuine and humble as a man can be. Gave me full access and answered all questions as best he could. Was proud of what little work he had done to the boat (new floor, little bits of cabin upgrades). Having never been able to sail the boat, there's little he could tell me regarding anything related to performance / seaworthiness / etc… He seems to be the 3rd owner…and I got the story of how it got to him: At his time of purchase, the then owner thought the boat may have been struck by lightning in a storm while moored and had the rigger at a Long Island marina go through the boat looking for signs of said strike. The rigger found none. Current owner says marina's rigger gave the standing rigging a good bill of health (chainplates, stays) except that the main shroud was 3/16" instead of recommended 1/4". This was 1.5 years ago. There is good stack of documentation that we did not have time to go through. You can tell it pains him to have to let it go and he seems to genuinely care for the boat. I like to think of myself as an empathetic person, but, I'm doing well to keep business and emotions separate.
Pros - She's pretty. She's clean… very clean, inside and out, lazarets to head. "Full keel" / non-centerboard, main traveler aft, tiller. Free of any hull defects / concerns. Looked straight to the naked eye. Paint looks OK but could probably use a fresh coat of bottom paint for good measure. Decks are solid, no soft spots, research confirmed that they're not cored. The Universal 3 cylinder diesel (age/hours unknown, forgot to ask) started up in 3 seconds from cold and was killed / restarted several times and purred like a kitten. Batteries well maintained as well as essential electronics. Very little slack in tiller / rudder. Prop spins nicely. No signs of leakage anywhere that I could see/stick a camera into (it had rained that day). No water in the bilge (thankfully since it has been on the hard for years). Water tanks are stainless. Holding tank plastic. Fuel tank stainless. Owner reports no leaks whatsoever from tanks. No fumes. All lines NOT led aft (hallelujah!). No crazing and only 2 cracks found in cabin fiberglass (corner of companionway on ceiling, and above port side ports at the curve of the cabin roof -- this last does cause a bit of concern as there looks to be water marks / stain around it).
Concerns - Being dismasted and rigged for transport, mast and standing rigging were hard / impossible to inspect last night (important bits hanging off the bow and stern a good 11 feet in the air, in the dark). Boom was free and looked good. Access to chainplates and through hulls from inside the cabin was blocked due to interior woodwork (see photo). Stanchion bases and other bolted hardware on deck showed signs of rust (see photo). A previous owner had replaced all ports and did a **** job / unfinished job of it on the interior; current ports are sealed (non-opening) and caulked/RTV'd; concern stems from the reason why they were replaced and not that they don't open. Winches have not been updated. Sails in questionable condition. Ancient roller furling. Will need new running rigging and possibly new / upgraded standing.
That's the short version of the long and short of it.
I'm now piecing together a financial picture of just what it will cost to: survey, purchase, insure, transport, step the mast, re-rig standing and running, launch, clean, paint, repair sail, find berth, prepare for everything to break, and stock the cooler
Unless some invisible-to-me-yet-glaring problem shows up, I think I'd be very happy to have this as a first boat. But, one careful step at a time.
Again, many thanks for all of your knowledge, opinions, and advice.