Had I hired a professional, it would have been done in a month and the extra five months of rent income would have paid for the contractor, saving me six months of nights and weekends.

This was buying dead brands where PROFESSIONALS in those particular industries in question couldn’t avoid bankruptcy and every single major brand in those industries failed to bid even a minimal amount to buy those brand names  - because they knew those brand names were worthless.  

Part of it is that for the longest time, it was considered professionally unethical for an architect to do any type of development themselves.

@Sean Relyea switch to a professional property management software system, Buildium, AppFolio, etc.

Getting an offer accepted and then negotiating a reduction based on the findings from the home inspection and/or appraisal.Offering my agent's commissionI would appreciate any guidance or suggestions to make my offer as respectful and professional as possible.

Consider Autohost or Hostfully both offer robust guest verification and deposit collection, tailored for professional hosts.

This year is the first year I will qualify as a real estate professional and be able to take some aggressive deductions through things like cost segregation studies.

It's usually much easier to pay a small monthly fee to have a professional manage your property.

That really is the only way to have an efficient professional partnership - total open communication whether the conversation is pleasant or sour. 

Because it's better to hire a professional agent to represent you.