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.

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.  

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

And those deals turned out to be huge equity gains 10 years later for sure. 

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

Mine is heavier towards real estate due to gains of the past few years.

We have a PMI of $250 a month and I’d love to get rid of it.I contacted the bank for a request for PMI to be lifted and they denied it.They said I could order an assessment of the house through them and then if house / condo come up with enough gained equity then it might be possible .Does anyone know the best first initial steps to order a home assessment ?

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).

Wanted to start a thread and hopefully gain some insight into folks who have purchased automotive dealership lot/store fronts and leased them out? 

FL appreciation - property is still fairly newish and don't want to miss out on potentially solid capital appreciation in next 5-10 years - assuming that happens-Other caveat is ability to sell in coming few months without paying any capital gains taxes, which will not always be the caseThere is no crystal ball, Appreciation is/was the goal but who knows if that will happen and at what rate realistically with increasing costs of ownership here.