I've never owned a rental so I'm having trouble guessing but I HAVE rented multiple house (active duty military I move a lot) and I've never seen my landlord dropping hundreds every month, usually zero dollars 95% of the time.

You are going to pay an extra 3.9% on investments outside of tax-sheltered vehicles (since Obama now considers you rich).Unfortunately, there's no way for real estate to lower your taxes.  

Lastly, the properties I buy, because I am not a big investor or a big fund, are usually outside of a metropolitan area. 

Also management companies who do this usually take a small security deposit.

I would look at it this way:On one hand, I can try to find a local bank that will like me enough (yes, it's a person-to-person relationship in these small banks) to give me the loan to refinance but they will do LTV or LTC whichever is LOWER and will usually use the current NOI as the bases of valuation. 

You have a pre-existing developed relationship with someone, that person might be willing to go the extra mile if you use that benefit sparingly.

From what I heard, redemption rights are usually bought at around 2k-5k, and in your situation it would probably be just for peace of mind.

as usual, my questions are very basic, so I appreciate your patience. 

Is it worth the maintenance and all the extra costs?

I don't mind paying extra for a quality report if necessary.