Put $500-$1k on 5-10 of them and hope one of the get you 300-1000% gains-- you still may be in a loss. 

This is the best place to learn and gain info, welcome!

I’m hopeful going into this slow season  because I have traction and great SEO optimization but can’t give any sort of projection at the moment. 

Closing four properties in less than a year exceeded my expectations, especially considering my initial hesitations.I am continuously learning about different markets and strategies, and I’m grateful to have gained enough knowledge that others are now seeking my advice.

The important points often glossed over are (1) is the buyer providing their personal guarantee to the seller for the note (2) is the seller maintaining a wrap position so they can foreclose in the event of default and gain ownership (3) is the buyer putting up additional collateral (4) how large is the down payment (5) what is the LTV (6) is this a personal residence for the seller or investment property (7) will the property cash flow and if so what will the cash flow be (8) is the property in a increasing, declining, or stabilized area (9) is the property being sold at market value, or above market value because of the low interest rate of the existing mortgage and (10) how experienced and what is the track record of the buyer, and is the buyer purchasing a property for investment or to live in or otherwise use.  

Advertising can be done on a STR platform, but will probably get more traction on websites where people are more likely to look for more than a nightly/weekly rental.

As a realtor and investor in Cleveland with a mid-term rental (MTR), I’ve gained some key insights from managing my own MTR, and I’d be happy to share my thoughts.

Does this also mean “selling” the property to the LLC and paying capital gains tax?

Your insurer gains a better understanding of your entire risk profile, which can result in more tailored coverage.

Haven't found much resources on how to structure the deal whether to buy out partner's shares at existing basis (I believe this wouldn't be advantageous as I wouldn't get to mark the asset to market and lose out on depreciation) or open new LLC or S-Corp and buy out both partners (I would end up taking gain tax due to sale but would get new dep. basis).