We BRRRR in San Diego county with outstanding success.  

You also want to be careful about outstanding rent/damages/utilities when the term does end. 

I think people have shifted their focus on quality of life and finances.

He has outstanding mortgages on both properties, so I thought about structuring a sub-to deal as I thought that the mortgage being paid would show as income that he doesn't have, while at the same time he's not the one actually making the payment so that he can receive the benefits, but that won't work as it would show that he isn't actually making the payment, but rather somebody else is.

I want to get a quality tenant, but I have zero pics to show.

Subtle increases will be more considerate of the tenants, but if you can still get quality tenants at market rent, then your best option is to raise rents to the market premium and give the tenants the option to stay or leave.

That would give you a huge return but it won't work because short-term renters will never rent your property because 1) it will be in a wrong location and 2) the quality of the property will be too low.

Depending on your area, these are becoming very competitive (there is still a huge demand) so it is important to weigh the quality of service/management in order to gain positive reviews and retain repeat customers. 

At about 10 doors you'll be ready for the conventional investment loan of 20 to 30% down, and by that time cash flow should be significant enough that you can start using some of the passive income streams to fund a higher quality, less frugal lifestyle. 

I'll echo what Kyle McCaw says about the shortage of quality professional contractors in WF.