I appreciate any help, guidance, or suggestions as this situation has gone on for so long that I have started to let my frustrations dictate my actions-Kate

A great tenant to me is one that can afford the rent first.Keep this in mind, if you start now letting your tenant dictate the rent, you will have set a president that they can make decisions about your rental property. 

If your handyman goes out there and fixes everything that needs to be fixed and takes pictures of everything, it's typically a better position to be in rather than letting the tenant dictate the repair/deduct arrangement.

Bottom line is the bank/lender and their appraisals will almost certainly dictate how it’s going to be.

Market will dictate that & my personal businesses, but that's a conservative target.

My lease also dictates the tenant is responsible for all expenses (legal and otherwise) borne from their lease violations.  

However, a lease that's ~$200 below market for two years, no security deposit, and then trying to dictate terms to me on how the lease will go didn't get us off on the right foot as landlord and tenant.

Don't allow this guy to be dictating to you what he wants - the building may be his, but the CASH is yours, and remember cash is KING!!

Your ability to anticipate, recognize, diagnose and resolve problems will to a large part dictate your success or failure in not just real estate investing, but in your personal life, as well.If this were all easy, everybody (as the saying goes) would be doing it.

dictates/allows.I like @Christopher Telles idea about writing to the broker (maybe even have a lawyer draft the letter; might be worth a few hundred bucks to give it that professional oomph whilst making sure you don't say anything that could expose YOU to liability of any kind?