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.

it would really become an awkward apartment if I tried to finish it. 

A garage I can convert, awkward layout I can reconfigure, etc.

I can be in crowds who I'm very familiar with, but with strangers, I can be awkwardly reserved. 

This seems easier with meals, hotels or rental cars where there is a per day cost that is easily calculated.Also, not to create an awkward situation, but it seems you both have a different take on whether the value of reward points are deductible (I spent ~21,000 points on Southwest and the ticket purchase would have been ~$250). 

I think it's awkward also because July is still a ways away to involve an attorney just yet?

Nothing to feel awkward about.  2.

Hey @Landen Gillis, Feel free to reach and I can show you how I find buyers!