Sounds like we are in the same boat with a handyman :) And to @Jonathan Klemm point, I have to weigh the mental capacity of handling issues remote versus spending time with family.

Talk with these folks and have them address handling the above.  

He has a staff of 3 or 4 assistants to handle the details, and his break even every month is $30K. 

If you feel that youre equipped to handle this, go for it; if youre not sure, then start with baby steps.

Is there a point of contact person/business that handles all home investor concerns (general contractor, engineer, etc.)

Is this an unreasonable request of my property management company, or should I expect them to be able to handle this with my rental's neighbor?

Quote from @Jaycee Greene: @Basit Siddiqi How about I suggest 5a: Do what 5) says but add to it, "hire a Fractional CFO to handle most of this"?

I think the VAST majority of successful evictions are for failure to pay and those evictions should cookie cutter and simple to handle for the most part.

I've been facilitating exchanges as a QI for a long time and the two options above are how we handle the situation. 

Management & Leasing FeesManagement Fee: 10% of the monthly rent = $180/monthLeasing Fee (Tenant Placement): 60% of one month’s rent = $1,080 (one-time)Lease Renewal Fee: $250 per lease renewalUpfront & Annual FeesOnboarding Fee: $350 (one-time for setting up the property)Annual Administrative Fee: $45 per year (for statements and 1099s)Reserve Fund Requirement: $300 (held for maintenance and expenses)Maintenance & RepairsOrdinary Maintenance: Any repair costs exceeding $300 require owner approval.Emergency Repairs: Up to $300 without prior approval; HVAC, plumbing, and electrical repairs can go up to $500 without approval.Home Warranty Claim Handling: $40 per claim (if applicable).Multiple Quotes Request Fee: $100 per request if you require multiple vendor quotes.HVAC Filter Supply Fee: $195 per year per HVAC unit.Repairs & Improvements: 10% markup over vendor invoice cost.Additional FeesInterest on Unpaid Sums: 10% late fee with a $39 minimum per month.Paper Check Administrative Fee: $20 per check if not using direct deposit.Insurance Documentation Penalty: $40 per month if proof of insurance is not provided.Eviction Protection Program (Optional): $15/monthProperty Damage Protection Program (Optional): $25/monthTermination FeesEarly Termination Fee: Equal to the management fees for the remaining lease term.Vacant Property Termination Fee: $500 if no tenant is in place.Transfer to Another Manager: $500 file transfer fee.