That can get a little heated depending on the bank/lender.

I guess it depends how the new assessments compare to how you currently value them.This is our tax appeal guy https://www.utbf.com/attorney/john-k-fiorillo/

How much depends on the answer to the questions.Why does the handyman need to book the repairs over 3 days? 

In an  Office or Industrial project, competing business can co-exist as neighbors because they are generally providing a service for which the "playing field" is away from the property.

Entitlement might get tied up and you might end up needing a down payment though depending on loan amounts.Yes, you could also have a VA and an FHA if needed.

Does it depend on the Amount in repairs that are required per the Appraiser ?

Would this be something that could hurt the legal protection between personal and business? 

Depending on the location STR is going to make the most money because condo rentals are an attractive option due to the amenities.

If we then have another meeting that we are pre signed up  and have paid for which is on Wednesday, the expenses that my wife and I incur on Tuesday are deductible because it is considered a work day since it falls in between 2 separate days of meetings that are directly related to our business.  

If you have a business that you invest in passively, then the profits from that business can be offset by the losses on the real estate.