We rent out the bottom unit LTR with long term tenant and are looking to move out of upper unit and make it a mid term rental.

An LLC doesn't provide you the ability to deduct something that wasn't deductible before.You also want to be wary of 2% itemized deduction which is what you are describing a lot of your expenses.They are currently non-deductible at the federal level.

In an urban market, level of finish and proximity to an attraction or location contribute significantly to demand for a specific home.

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I'm not sure I'd have a PM oversee another contractor but I would probably have them involved at some level especially if you are working long distance.

This isn't a free weekend seminar, it's $10K to $30K up front.But let's assume that they are on the level.

We are pursuing a house hack (fixer upper) and turning the basement into an ADU which we rent on Airbnb.I had a theory that Airbnbs that performed needed to be walking distance to a metro.

I am considering building a rooftop deck/rooftop terrace on the rear side of an upper level addition. 

All cost seg companies will eventually point you back to having that conversation with your accountant, so starting at the accountant level is going to save you time