So far I hear crickets... with an occasional moment of interest that usually turns back to the owner putting the effort in to sell their house on the retail market.  

Including real estate :) but yeah occasionally if I’m sleepy it can seem longer

But if he's basically reliable and completing the jobs when you need them to be done, then I wouldn't be upset at him wanting to start late, especially if it's occasional. 

Upgrade occasionally to justify needing to do that every so often to justify your rent payments. 

Teachers, nurses and grad students often refer other qualified friends in the same fields to become new tenants.If everything is running according to plan (an you are keeping your contingency/replacement funds growing to deal with the occasional emergency) I'd suggest you think long and hard before selling or trading this known entity for the next unknown one.Good luck.

Occasionally if I could not find the right person at the lender, I would try with the substitute trustee.   

There is usually very little available in that range, maybe the occasional one br condo or house that needs to be rehabbed from the studs or torn down.

I work for a large national bank currently but am looking to start investing in real estate, either by house hacking or by using AirBnb to occasionally rent out a room.

Most of the houses built in 1990 or newer are going to have a price of $150,000+ in those areas but you can occasionally find one for less if you can move quickly.

This is a really neat feature because they don't require constant access to wifi and only use it for occasional updates.