Currently have a 24 year tenant, who has agreed to a new 3 year extension, where they take care of all utilitites, lawn service, snow removal and minor maintenance up to $400. 

Do that and you eliminate the risk of bad tenants, maintenance, etc.2.

All you need is a single place to track tenant information, payment history, maintenance, and other things.

You can buy something like a cheap Arlo camera system at Costco and pay for the Internet connection in one of your units.You could ask law enforcement to do routine drive-bys or safety checks.

Are they putting you in touch with their "team" i.e. cleaners, maintenance, etc? 

And are there any increases in maintenance or other issues you've experienced with the transition?

Is item "Repairs and Maintenance Furnaces" just for the furnaces, or for ALL repairs?

On the other hand, single-family (typically) provides a tenant pool that can be more manageable and longer leases, and I am assuming maintenance and capex could be on a smaller scale, but I could be wrong on that. 

My guess is one fee you and your friend are noticing is a percentage cut from third party maintenance work.

Hi John - We do have one property that will not be profitable or just about break even in 2024 due to all the unforeseen maintenance items:  pool heater, roof, pool fence, handy man over a dozen times, remodeling took 3 months instead of 3 weeks, etc.