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 only item I changed my mind on is shuffleboard.

Those last items are strange sounding to me.

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). 

You are paying what you would in rent but also capturing the benefits of owning (Loan paydown, appreciation, tax benefits). 

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.

Glen, I'm not aware of a way to automatically categorize items.

One important item to note: if you receive passive losses from bonus depreciation and do not have a use (or only a partial use) for those passive losses in that calendar year, they can be used in subsequent years to offset gains as well.

I have assumed their leases and added an addendum that includes a few items (no auto renewal, new payment address, etc… ) which I am planning on asking them to sign.I sent non-renewal letters about a week after closing (early April), which gives them way beyond the 30 days' notice.

I send my Tenant an itemized list of charges as required by law.