We never hired a management company, as it was not cost effective with rent we have been charging and it is only one house.Another question: If I do wait til Fall 2019 to sell, should I rip the carpet (up the stairs, living room hallways, bonus and bedrooms—2600sf house) and leave floors bare, (it’s light colored, horrible carpet) to allow buyers to add their own?

This is a great reason to hire a seasoned property manager. 

Since I don't have an agent to guide me thru the process do I need to hire an agent myself, do I need an attorney?

Perhaps a nice 1950's built bungalow.Always hire a 3rd party property inspector to give you an unbiased feel for the home.

I lived in HB many years ago (last century ;^) ) and the moist ocean air was always present.

I will say that you more or less have to keep up with air B&B to keep that property cash flowing.If you intended on living in it, I would say its probably a pretty decent start.Be a little careful on that stretch, some of it is pretty good, some of it is a little sketchy.Having owned a duplex pretty close to there, I would guess (without running the numbers), that the initial return would be just so/so. 

We're doing well in Ch-ville by buying fixer-uppers with cosmetic re-habs needed and Air BnB'ing them.  

(They were knowingly bouncing checks and made a claim of ownership, blah, blah, blah) I have a very good attorney that I hired using their funds (their Option fee).

There's the whole "cranes in the air, buyer beware" adage so would now even be a good time to house hack if downtown homes are going for a premium?

Obviously, I'd need to hire a property manager if I went this route, but I'm curious to hear the challenges, or benefits, that come with long distance investments.3) Is "retiring" and living off your rental portfolio a realistic goal?