Chris, you're not alone in other ways too. Many of your internet friends around the globe feel your pain, and have either been there and done that, or are presently faced with the issue now.
Charles, in Martinique, had a heartbreaking issue with his 427 rebuilds, for instance, and many people pitched in to offer assistance, advice, and in my case, actual parts sent from Nashville to help.
Boating is where you first have to make the darn thing float. Then you punch holes in the hull, run a prop shaft that has to turn and still keep water out, and put a motor inside that has to run like its on an uphill run all the time. Add explosive fuel, confined quarters, and the entire need to add style, gleaming wood, function and safety, and it's just nuts to begin with as a basic concept. But there are many out there with everything coming together, and when it does it is a ton of fun.
I am really glad to hear you're planning on doing the slow cruise to Huron. I think that will be very gratifying for you and Cindy to get the compliments from the Commander group, and for everyone to see your work. The boat will get a lot of coverage too. At that point, you'll either decide to keep it, or turn it over to someone else. I understand, life goes on, people and things change, nothing stays constant very long, not even the rocks (that's where sand comes from).
All of us who have messed around with boats, cars, motorcycles, very long have had issues like this. Did I tell you about that Alfa Romeo cylinder head I had to remove (twice)? When they go, they bend all the valves too. On that issue, I have nobody but myself to thank too, because it was poor work on my part that caused the problem, and it sure was a learning curve for me, in more ways than one!
On your SBC, hauling one of those out, popping in a new one, is not the end of the world. Neither is running the boat another couple years and having to do the same thing on the other motor. For the price of a long block, you could buy yourself a really nice 38' Commander Sport Fisherman. On your trip to Huron, you'll have time to ponder the alternatives.
I am really glad to hear you'll be there, with or without the boat, but preferably WITH the boat. I'm looking forward to meeting you (and Cindy) in person, and looking over this magnificient 38 that I have only been able to associate through your generous photos and postings.
All the best, onward and upward!
Paul