None of your items are that big of an issue for me.

I've only had a few maintenance items that have come up, but that goes along with owning rental real estate. 

Upon the sale of the condominium, the capital gains on Person C's sale would be calculated as follows:A. 33.33% of the sale price minus the original purchase price to account for the interest acquired via quit claim deed on July 7 2015.B. 16.66% of the sale price minus the stepped up fair market value on 11/17/2020 as capital gains for the 16.66% remainder interest acquired on 11/17/2020 from Person A.C. 50% of the sale price minus the stepped up fair market value on 01/17/2023 as capital gains for the 50% remainder interest acquired on 01/17/2023 from Person B.Total Capital gains would be the sum of items 3A, 3B and 3C above minus any allowed deductions, such as the home sale costs (closing, repairs and so on).As an individual owned rental property, upon sale the only way to avoid the capital gains would be to do a 1031 exchange and then hold the new property that is purchased for approximately 3 years before selling it. 

You should be able to charge for any of these items if you have receipts for the expenses. 

While I am capable of holding onto a property like this, I fear for the newbies who have very real risks of not being able to hold onto the property long enough to get out from underwater.Because the buyer of this property is likely to be inexperienced and not know or think through all of the items discussed here, this strategy may put you in a ridiculous position of power for at least the next decade over the buyer. 

The how has always just been a detail found along the road, never laid out ahead of time, just an item to solve and over-come along the way.

The only item I changed my mind on is shuffleboard.

Some optional items from a LTR lease now become requirement: you have to own the utility account, definitely have contractors to maintain yard, pest control, periodic soft wash the exterior, pool/hot tub (only speaking from FL, or any other property routine maintenance in other region). 

Those last items are strange sounding to me.

I am considering how hard it is to collect anything when theres a problem. how much the deductible is means I’m already covering all the smaller items.