Should I sell or keep my rental?

[Robert Morse]

Hey all, I've been poking around this site awhile now and it's causing me to take a long hard look at my current strategy. I own a townhouse in southern Maryland (Great Mills), that I paid $140,300 for back in 2010. It is now worth a whopping $141,000 according to Zillow and I still owe $103,000 on it. I refinanced into a 15 year loan back in 2012 and I'm paying $600 every two weeks on the loan (the minimum payment a month is close to $1100). My goal is to get it paid off by 2025 and would love to pay it off a lot faster. However, I'm only currently getting $1050 a month and I also have a $600 a year HOA.

I'm renting the house to my friend who is doing all maintenance and upkeep, and has been renting it for the last 3 years.  I'm losing money each month but it has been a hands-off rental for years.  He has done repairs on the house out of his own pocket.  When he moves out (which might be in the next few months, pending him getting a new job), I should be able to rent the house for $1200-1300 a month.  My goal is to have several houses paid off and generating cash flows.

In your opinion, am I better off selling the house and trying to find a rental with better cash flow?  Keep paying the house down (I'm currently paying my car loan down as aggressively as possible and will then take that money and apply it to the mortgage)? Refinance into a 30 year to increase my cash flow (current mortgage is only 3.125%)?

Any and all advice is welcomed.  Just not sure if it's worth keeping or if I can achieve my goal of having multiple income streams (replacing my current income from my job) faster by selling.