You could get a HELOC in it (as long as you are still living there) and use that money to do some other investing. 5 years from now the beach house could be worth as much as $1.5M which would make for a great $1M 1031 exchange into a small apartment building.

If not, you may want to take a small risk and put the money in an after tax brokerage account and invest in some index funds.

And I get it; living in a small town means these are people I’ll be seeing all the time anyway, so making peace with that is part of the game.

You are correct, small multi listings in A/B markets are less common, but do come on occasionally.

You will have a pipeline.If you cannot do 5000 letters a month, do what you can whether its 3000 or 2000.When you're doing a small volume of mailers like 2000, I would make sure your list is actually big enough.   

However, since Seattle turned against small landlords I have sold many(taking the tax hits),  getting out.

This depends on your agreement and whether you are hypothecating the note (meaning you own the note and are borrowing against it) or doing a partial where you are selling that portion of the note and issue a collateral assignment.When i did partials I did it as a hypothecation where I kept control of the note because those who typically buy a partial are not savvy note investors and if it went into default the first call they would make would be to you.I know some who let the buyer own it and they would be calling the servicer every week asking about payment or emailing the etc. then if it did not show up they would be calling them.How you structure it is up to you, just realize there are pros and cons for both hypo is the way to go.. also the OP might just check with their personal banker if by chance they bank with a small community bank..

I’ll likely close on the property around early November and it will need small cosmetic updates, maybe a new deck, and of course new furniture set up.

It’s a small single family three bedroom one bathroom unit, I bought it for cheap and plan on renting on the higher scale by making minor improvements such as flooring, fresh paints and of course new kitchen and bathroom

We paid him in installments and we're at our final stopof rebuilding our entire kitchen and finishing up small details like filling upnail holes, bathroom vanity installs and etc.