Whether you screen well or not finding decent tenants is a stretch.

You can draw inferences from more holistic data, but this is a pretty Stretch Armstrong level stretch to me. 

In our building that I wouldn't call luxury by any stretch, the eleven other units all pay the same and we also have a liquor store downstairs that also pays rent to the landlord.

Not realistic by any stretch.

If you are confident the extra unit won't stretch you too thin in finances, experience, and time, I'd say that's the better launch pad!

They do not do that 5-10% stretch in value to accommodate like they do on purchases so be wary to have solid comps for that cash out refinance when it comes around if you chose to still go with conventional financing route.

It does stretch my mind to ponder paying above the comparable sales value though. 

Transitioning long-term-rental spaces into short-term-rentals (STRs) can be an excellent way to stretch around uncommon challenges, even if on a provisional basis.

Many of us have done it when we started out.I don't know what your day job pays, but if you make a decent living, try to buy the nicest fourplex you can that's under a half million (that's the max you can afford on 20k, and even that's stretching it).

I can stretch out and put 15% down but 20% is out of my range.