Hey, Jeff, thanx for the very articulate info on old fiberglass ... sobering to realize how exactly you've described our 1980 CSY in that summary. This is supposed to be our 'forever' boat. Sigh.
Thank you for the kind words. I would not get discouraged.
Here is the thing about a boat like yours,she functions well for your needs and is structurally suitable for how you are likely to use her. Boats like yours will remain functional and useful long after the latest performance cruiser or race boat becomes relatively functionally obsolete.
The down side is that the market for boats like yours ( i.e. quite small, older, live aboard cruisers which sail half way decently) is comparatively small, and it is that alone would tend to hold the price down quite a bit. On the other hand, when you sell a boat, you are only looking for one buyer, and the right buyer may pay more than the average buyer for a well equipped small cruiser in decent shape since that is precisely what that particalar buyer is looking for.
But in the end, like most things in life, it is how well your boat suits your needs. In the 1970's my dad and I owned an old wooden boat together. Most decent sailing days, I would get home from work, peel off my work clothes and run down to the boat for an evenings sail. We had bought that old girl for something like $2500. There was an older man in the next slip who sailed with me often. His boat was worth 30-40 times what Indian was worth.
One day he commented that for our meager investment, we enjoyed the water no less than he did. And that gets to the heart of this discussion. As long as your expectations are reasonable, then there is nothing wrong with owning an older boat
Where I often disagree with the court of public opinion is that not all used boats are made equal, nor are they always as good as the court portrays them, or sail as well as other, better designed, equal age boats, or for that matter, are seaworthy as better designed equal age boats. I my usual criticisms, I try to point out the relative merit of these boats and urge folk to make reasonably informed decisions and if they are going to go through the work to restore a boat, then buy the best design that they can, since it takes little or no more work to restore a junky design than a really nice one.
So enjoy your boat, take the value out of the joy she gives you, and do not worry about the rest.