I’m spooked because a house hacking friend called to ask his HOI company this same question before he started renting out rooms, and they just flat out dropped him.

I am starting to see at least a few deals that seem to make some sense.  

Most of our guests are looking for an office for WFH I haven't started renting yet.

Novice “future” landlords here—Where did y’all start with getting your lease and even a property manager? 

For example, if it was a ten year lease starting in 2017, then you would need to honor it through 2027 - if there was also tenant options to renew then those also would need to be required to be honored.

@Cody RigbyThat's a great starting point for your real estate investment journey!

Even though I claim in long term returns will be similar and the effort will be less in the high class area, virtually everyone starts in the better cash flow areas (working class areas). 

Because I live in MD, I want to start investing in that market or in DC, because I feel I know both markets.

A sale removes both burdens and allows you to start over fresh and focus on more than one purchase.

If not I would start there, but also look into creative finance.