Downsizing -- pros/cons?

I can never get rid of my books and required a library room when we moved to this house. DH wanted a wine bar, and he also needed an office, so we turned this room:

Into a combination space that comfortably houses our books as well as the things DH wanted:

We have customized this house so much, it will be very hard to leave, but we don’t need all of this space (or the type of HOA we have), and I keep thinking that we are going to right-size once more now that we’ll be in Maine at least five months each year. I feel stuck, though, because I don’t want to pay the going rates for what will surely feel like less, but I keep looking.

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