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I haven't advertised a rental on Craigslist since 2010 and it was full of scammers and other problems back then.It's hard to believe that site ever survived.

I also own another unit in the same building, and no other tenants have ever complained about inadequate heating.I’ve advised her to keep the heat on 24 hours a day, as the lease specifies that the tenant is responsible for paying for heating costs.

First car I've ever had that went up in value. 

Landscaping will have the largest effect on the resale value vs a kitchen or bathroom.

Don’t ever invest and hold.

If you ever read the side of a Heinz Ketchup bottle, it reads "Do a common thing, uncommonly well".

Quote from @John Underwood:He still to the day says this is the worse thing he has ever done in his life I was told many times growing up (and repeat hearing that voice as an adult).   

What happens with the capital gains taxes if this is done ... do they just disappear forever or will I only ever need to pay them if I sell this house? 

Even then I'm not sure I would ever put one in an STR.