For me, it's hard to put a price on the reclamation of _time_ spent otherwise thinking about those issues, to say nothing of the money. I just don't have time to think about even 1/60th of what's involved in getting vendor quotes for roof reshingling or painting or whatever, and even if I do have the time, I'd rather pull my fingernails out than spend it that way.
I sure do miss that mortgage interest deduction, though. I had no desire to accrue equity in the property--and indeed, if I had more equity, I would have lost even more money than I did in the 2008 crash--but I loved my super high-interest loan. It meant that my most of my housing payment was tax-deductible, and that's fantastic. My only regret, besides buying itself, is that I didn't take out an interest-only mortgage.
However, this isn't a Great Recession sob story. The condo would be way too much work and cognitive bandwidth theft even in the best of times, and that's like a tenth of the structural, landscaping, etc. issues one has to think about with an SFH. No thanks, man. I have other stuff to do.