Has anyone successfully hired someone to perform some of these routine duties?

If they've owned rentals in the past then most likely they know the routine. 

Part of my routine.

BTW some of those REITs will absolutely blow the doors off in profits compared to what some others routinely call passive in the rental game. 

caused us to seek legal advice, so we know that routine.

Keep in mind just needing to replace the roof one time within the next 10 years or so could wipe out whatever savings remains in your repair budget after paying for routine maintenance, leaking faucets, landscaping maintenance, snow removal etc... 

Banks will routinely audit to see who they might be able to get more money out of & if it's a non-disclosed material change to the original lending agreement and they did not expressly agree to the change in terms, they will want to change the terms to make them beneficial to the bank.Also, if you do not have credit built up in that entity or equity to leverage, the chances of you getting a sweetheart rate are lower compared to your own good personal credit.   

TTax allows multiple returns.I'm headed to the bench now as you've exceeded my risk tolerance and street knowledge since I would rather pull out my eyebrows than co-own real property with a unrelated party without a multi member LLC or a partnership with a CPA and attorney already in tow... 

If you have a lawyer that routinely handles these types of lease negotiations, you should be fine without a broker, but one way or another, you need someone with insight into the current market for lease terms. 

(Source: Investopedia).As a former banker, we did these type of loans on a regular and routine basis.