My experience in Chicago, which is obviously a primary market, would lead me to believe that there are simply more agents who know what they are doing in a large metro area. 

My sister-in-law turned on the oven and melted my mandolin, my father-in-law melted my cutting board.

Obviously, being on the deed would qualify you as an owner of the property but what about simply being under contract?

You also have it on a 15 year note, so cash flowing on  a 15 year note simply wont happen, so that should be taken into consideration that you will pay this off rather quickly.

You are in business, you are simply operating as a "Sole Proprietor" Yes your expenses are deductible.

can I simply raise their rent as I slowly renovate?

I have to imagine that it is simply not worth it to most people for $50/mo!

Here's my concern about simply waiting:1) I don't learn anything from waiting.

Rather than cut out an activity, people more often downsize.

So for example, rather than having a 7-year fixed commercial loan on a 30-year amortization schedule, are banks willing to simply do a 15-year fixed commercial loan on a 15-year amortization schedule?