I don’t live in the USA all the time (< 1 month last year), so coordinating non-trivial refurb may be awkward, not sure my old handymen etc are going to be available (or suitable) so perhaps something a little more turn key is suitable.

It can be awkward having to tell them to keep it clean so you just set ground rules in advance.

As an aside, the old management company (that I terminated a couple weeks ago) gave the tenant my personal cell phone number so I got a call from her yesterday which was awkward and highly unprofessional. 

I house hacked with 4 roommates (at one point split my bedroom and had a 5th roommate) and it wasn't fun, came home and had to deal with issues, fixed problems, had some awkward/difficult encounters, but it was all part of the process and well worth it. 

This RV area is located on one end of the property where a mobile home used to be and is right off of the private road, but that area is very narrow and awkward so building there wasn't the goal. 

It does make it awkward, but you'll just have to do the best you can. 

It'll be awkward and may feel like you don't belong but in my experience everyone is happy to share what knowledge they can and possibly give you that mentorship you're looking for.

I'm lucky to have a job where I can start early and be off at 3pm everyday with no weekends and I can pretty much take off whenever I need to.  20 units is just an awkward phase where I don't think it's worth having a property manager, but it's also getting to be much managing on my own. 

When we get awkward 2-3 week gaps and have to switch to an STR model, it's a PITA because we're cleaning ourselves.

He did a fairly decent remodel and converted an awkward cut out in the floorplan into a functional den, making it a great home office for future tenants and resale.