Quote from @Jonathan Soto: great write up. thank you for taking your time and going in to detail. i have been looking into a business for myself but havent seen much in biz bysell that make sense. just need to keep searching Try looking into Crexi and Loopnet too, I find all different kinds of small businesses for sale on those websites compared to Bizbuysell.

However, if your income can't support the debt of the mortgages plus whatever else you may have (car loan, student loans, etc) then you may NEED that lease signed in order to offset some of the debt.

I kind of gave up on Stessa, just do not have the time to deal with ongoing computer issues and constantly not being able to communicate with a company.

Feeling uncomfortable with sellers stems from some kind of fear. 

I've always worked for myself and didn't have a ton of support so I was not able to prove my income for quite some time due to doing my taxes wrong or not understanding how things work.

Quote from @Andrew Syrios: So basically note investing is really trashy and you're looking for a continuous stream of income but instead of alimony or child support it's loan payments instead? 

I'm looking at working with insurance companies/temporary housing for my next rental, I have an LLC, but I don't know what kind of credibility they look for since I only have my personal residence that I house hack.

ALSO they have regs on rooming houses only allowed in specific zoning, similar zoning as for hotels;  only on main streets in business districts AND you have to apply for licensing and blabla as for a hotel..That said;  there is a small movement supporting rent by the room as a small step toward solving affordable housing. 

Maybe I missed it, Bill B kind of eluded it but why not do seller financing? 

You have to look at rents per sales price in both areas and see what kind of return you can get versus what you are getting now outside of real estate.