I talked to a commerical RE lender who does the Freddie Mac Commercial loans and his sample loan doc has the following language:Non-recourse to Borrower and Guarantor(s), except for standard Freddie Mac recourse carve-outs.The borrower is the LLC, and the Guarantor would be me.

Instead of lowering my standards on background checks, I waited a bit longer for the right tenants just like you suggested.

I would definitely recommend screening tenants as a standard practice for your own protection, regardless of whether the insurer requires it.

If you provided AC, then your obligated to keep providing AC.Service call fees are standard for pretty much any type of contractor. $200-300 is typical in the larger metro areas.

There are also owners that buy at $30,000 home that is dilapidated, in the worst part of town, and not in rentable condition to anyone that has a job or just standards in general.I suppose there is the chance that you were done wrong by 5 property management companies, and had a run of horrible tenants, but I would wager a guess you got what you paid for. 

is it standard practice to charge it from the tenant in addition to the rent?

Since you bought this for $5k less than the appraised value, I don't think there would be a big enough jump in adding value where you can do a cash-out refinance, and you would likely be bringing money to the table to pay off the HELOC with a standard refinance. 

Mortgage interest is only deductible if you have more "itemized deductions" than your "standard deduction."

Your attorney's advice aligns with standard practices to mitigate risk.

However, here are some considerations:Permitting: Unpermitted structures are often a red flag for lenders because they may not meet local building codes or safety standards.