Ones who will manage in the worst of areas I've found have a direct correlation with poor performance, poor tenant treatment, greed/borderline steal, etc. especially as a small PM company scales.

A common setup is a multi-member entity with pass-through taxation but your investment plans could call for a different entity type and different tax treatment. 

These are just estimates of cost Both Roofs- $20,000Boiler unit 1 replaced installed $10,000Hot water heater apt 2 (28 years old) $2000wrong door/fire proof door- $500Termite treatment $1000Electrical box wiring wrong in garage ?

In reality, lenders should permit a large portion of this to be added back, as they do with typical depreciation (whether you agree that is correct for a bank to allow this add-back or not).(2) Converting personal expenses to business deductions, whether it's the proper treatment or not (home office dedutions, meals, travel, cell phones, etc.)I would work to become bankable as soon as possible.

It is a roof treatment spray to end the life of old roofs. 

(Count on the cost of a new roof/5)  How much a typical Roof Maxx treatment(?)

We were able to replace the siding and the roof on the entire house, new A/C unit, rehab the entire interior (fixed foundation, new floors, paint whole house, new kitchen, new baths, install ceiling fans, reglaze windows, termite treatment, etc) for $50k.

This post should helphttps://www.biggerpockets.com/forums/530/topics/1056436-clearing-up-confusion-on-tax-treatment-of-short-term-rentals

My pesticide guy prefers the plastic as its easier for him when he treats, and he did the plastic when he was doing a termite treatment. 

Unless he is providing more than you in terms of scope of work or capital, then he should not get special treatment as a tenant.