And with the five investments we made in good parts of our town, that even if all our efforts in the business didn't pay off, in 20 years we'd still have a nest egg of equity we could fall back on.

You can try to outsource that experience to general contractors, property managers, agents, and others (I highly suggest you do), but all of those services will eat into the last "R" of repeat. 

Keep it up and you'll have a nice nest egg!

Short term guests are frequently on vacation, and are outside of the house a lot of the time, sightseeing, eating out. 

I am specifically interested in housing women who struggle with eating disorders.

If the repair will eat up a few years of cash flow, I would just sell it and reinvest.

Or offering personalized consulting, deal analysis, or portfolio review for an additional fee (as others are doing today).Your comment makes me wonder if we have a "chicken and egg" problem in the note-investing market.

If someone is buying a $200,000 to $1+ million property, all those fees will eat up any rental income and any "tax savings" is obliterated.

Someone will buy that, and then have the pleasure of mowing or more fun-weed eating that to keep the city off your back.Not sure about SD, but I tell everyone you need time and money

They could buy now, but they would make less and would have to eat the cost of refinancing down the line.