If the property manager uses a payment app integrated with the property management software to collect rent for the landlord, this is not gross income for the property manager.

@Rafael Ro have you thought about passive investing in syndications? 

If not, the income won't be considered. 1.

However, this would force them to move out, lose their current rental income, and have to pay rent off their limited salary. 3.

This is easy for some people that have lots of friends investing in passive real estate opportunities.

The rental income from the first home will pay for the mortgage/monthly costs.  

So more Roth for way less in taxable income incurred. doing this is easiest in a Solo 401k if you qualify but can also be done using a checkbook IRA as well. check out this post that @Dmitriy Fomichenko made explaining this concept.https://www.biggerpockets.com/forums/51/topics/1223601-how-t... 

Find out through asking the right questions what will help solve any existing problems, that will give the seller a nice monthly Passive Income Stream, etc. 4.

I have  a W2 job and look forward to the losses this year to offset some of my income (Not my 'WHY' for running an STR, but a nice bonus).

Excluding the periods of “tulip bulb” irrational exuberance, a property must produce enough of a risk adjusted return to satisfy both the ROI demands of the “limited partners”, and the income/time requirements of the sponsor.