My primary focus is going to be on buy and hold properties in order to generate cash flow for the future.  

,Financing $250K to generate a gross of $2000/month seems a little risky. 

Here you have a choice between tax on income (i.e. a flip where the property is considered inventory) or capital gains tax (on an asset purchased for the purpose of generating passive income ... i.e. buy and hold).

I'm curious if anyone has ever successfully pitched a mortgage lender an investment property on the basis of the potential income it could generate from Airbnb, VRBO, Flipkey, etc.?  

If I had any hope of providing my parents with a remotely stable retirement, I had to generate some wealth.2) Equally as important, I wanted to prove to myself that I could.

And a separate lot will generate more value.

Quote from @Kate Schaefer: I screen my applicants through a system that gives a custom score, but we ignore it and generate our own score based on credit history, income: debt ratio, Landlord references, etc.

This would generate about $2,000 monthly positive cash flow (I realize this resets my terms and back at a 30 year mortgage).I checked with some other lenders for my rentals and they can only offer me a 5 year fixed term that can be renewed or a 30 year term at 4.95%.What are your thoughts? 

In today’s COVID environment I’m really looking to minimize risk and I would much rather have an empty house not generating income than an occupied house costing me money to get it back.  

Another consideration is a cash-out refinance on the property to tap into some of that equity AND generate rental income.