As a lender, every FSBO I've done has been quite painful.

I'm only trying to fix the situation I'm in now.That's a painful experience.

Travel to get the feel Once done with 1 and 3,  fly out in the area and spend few days to drive around neighborhood and take notes per home/block/street on what I feel.

It is a 100% pain to get a loan self employed3) Would not be an issues.

It's a pain but the post office has a sytem set up for it.I told the tenant I couldn't do anything for him until AFTER Memorial Day and after that I would figure out if we had a spare and get back to him, , but I told him to in the meantime, call the post office, hold the mail, and manually pick it up, and keep looking for the key.

For at least half of nearly forty years life I've lived and invested in property within a block or short walk to the beach in South Florida, Southern California, Southern Oregon and Northern Baja Mexico. 

There is aircover which essentially is guest damage insurance but it's an absolute pain to deal with and get money out of Airbnb.

Our plan is to sell or refinance within 15 months targeting a sale price of 3.5 million.This property is two blocks from the beach and has a high demand for short term rentals.

Thanks @Jonathan Klemm. it's just couple of blocks west of palmer square and there are standard size new constructions selling for around $1.3million.Just closed on the purchase and it's a 40 feet wide lot.

But a pain on the back end.