I do feel comfortable sitting in the same room as him so that should've been a dead giveaway.Developing takes schmoozing and baby kissing.

Only you can decide where your comfort level is, just make sure you understand the risk balance. 

-Setting Criteria: Defining specific criteria such as location, property type, Financing Options (Including Seller financing), and comfort level to narrow down options.a.

I think it is dependent on your comfort level with the tenant. 

“In 2020, a household earning $59,000 annually could comfortably afford the monthly mortgage on a typical U.S. home, spending no more than 30% of its income with a 10% down payment.

I'm not comfortable buying a property with a negative $500 cash flow hoping future appreciation will cover the loss. 

I understand that in the long run, the property may appreciate more, but are you comfortable paying $915 out of pocket each month?

I've spent a lot of time researching rental properties and was comfortable with that strategy, but since nothing pencils and I'm pivoting a bit at least to get started, I feel like I'm starting over before I even began. 

For 90% it does not make sense.Most guests are not comfortable booking outside of Airbnb. ...Yeah, that's a side of this I haven't even thought about.

Im much more comfortable with 15 year mortgages closer to 5% or under (not going to dream about the 2-3% rates  pre pandemic).