Brokers are best-suited to look at the specific situation and find you the right fit, not just whichever lender says "yes" first. 

Hi BP community,I'm hoping I might be able to get some feedback and clarity on a situation I'm providing help and moral support on.

I don't want our situation to stop us from investing in real estate.

Regarding the roomate situation, my agent told me the insurance will likely cover the property damage caused by the roomate,but if he got injured due to my liability, that won’t be insured. 

I have relationships with mortgage brokers and will set up my potential tenant with a broker to evaluate their financial situation to get them ready to purchase in 2-3 years.

Unless you're willing to invest in this for a loss as an autonomous learning experience, get someone.I should add that all my impish personal demons are whispering to me to tell you to just pick up some spackle at the dollar store and go for it.

I have an interesting situation on my hand, one of my rentals (Townhouse).

I recommend you talk to them as they will know your personal situation better. 

Each situation has to be analyzed on its own merits, and certainly for your area.

There's no net income in this situation.