Grew up in Cedar Rapids. Where do you call home?
What is your past sailing/boating experience? Have you lived on a boat before? If you have limited sailing or live aboard experience perhaps you might consider a longish charter and see if that is something that you want to do. If you have a bunch of experience then you probably already know what you want to do.
I cannot disagree with your logic on the depreciation of older boats and the thought that you may not take a large loss on resale, assuming you can sell it. My feeling is that the original purchase price on an older vessel is a very small part in the cost of ownership when considering: maintenance, refitting, insurance and storage. A spread sheet showing the cost per hour of actual usage would be interesting and possibly very depressing.

There are certain benefits that cannot be given a $ value for sure. Which leads me back to the idea of a multi-week charter if possible. Taking that one step further would be to charter in different areas, Mexico Caribbean, Med etc... Smaller scale might be a trailer sailor. Could take it anywhere you want to go. Some models seem to be livable for periods of time. If you decide on a larger vessel at another location you could still have a boat in Iowa for some summer sailing.