I would vet them intensely and make sure the lease is personally guaranteed. 

James has time and time again always posted extremely helpful information on every post, he would be a great person to connect with. 

Haven't personally used either but they are both on my radar.

Response to #1: Some lenders allow for layered entities while others want warm bodies/natural persons to be direct managers.

As long as the person hasn't used RAFT in the recent past then RAFT will cover up to $7,000 for first, last and security as long as they qualify.

My advice when looking at a house hack is to not get too in the weeds on how the property or building performs compared to other properties in the area, but rather view it from the lens of what it will do your personal finances and the impact it will have on your personal cost of living.  

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

I invested in 7 syndication funds in 2023 as a limited partner with the expectation that I would generate first year losses from cost segregation that I could use to offset my gains on my personal real estate investments (self storage). 

No there is still one person living there right now. 

Typically that's the roll of a business broker vs real estate agent, although sometimes one person does both.