The short answer: YES, you usually need to send 1099s if you're a landlord, regardless of the number of units.The confusion comes from the fuzzy definitions of "running a trade or business."

I bought 14 homes in a short period of time for gozone tax bene's those are the same as the benes that people search out for cost seg these days.. except they were much easier you did not need a cost seg report..

So you must buy 3 bedroom or less and you can only rent out 2 of them. https://files.lasvegasnevada.gov/business-licensing/Short-Te...

If your concern is cashflow, then your concern is about being short of cash at some point.

Short and I concur on your explanation. 

I told the manager I've managed a portfolio of short-term rentals and that my previous landlord allowed me to do it and loved that it created an incentive for me to take exceptional care of the property.

Do you have short-term capital to continue to invest in your next deal? 

You will need to have experience in short term rentals to interest a lender on this.

We lucked into a rehab project and successfully run a short term rental in Bell Buckle TN.

The short answer is I look for 9% min and try to press it to 11% with those strategies along with rental increases once improvements are made and the tenants know you actually care about the property.