I am confident I can capitalize the renovation/construction/zoning costs, but what about property taxes paid in 2018 (all of which exceeded the $10,000 SALT cap based on our W-2 state taxes, so none have been deducted). 

But you do not deduct it until the year of sale.

If I pull 100K from my house and then leverage that x 80%, then I get a total position of $180,000 and its only costing me 4.71% interest per year (fully tax deductible!).

I would trust them to do this as they have already been handling all the small maintenance themselves and organizing professional repairs when necessary, which we deduct from rent.

Therefore, my question is since I wasn’t able to do a Move-In Checklist, do I have any leverage to deduct from his security deposit if I find major damages?

I am wondering whether or not I can deduct entity creation expense on my taxes.

Or do I just deduct from sec deposit?

I highly recommend you to use your insurance to pay for the door if the cost to replace it is higher than your deductible.

I make good income now that I want to try to maximize my tax deductions as much as possible while I have high income. 

The management company pays me after they deduct any expenses and their management fee. .