Current investor needing some help figuring out long term plan

[Ashly B.]

Current situation. I own a 4 plex purchased in June 2015. Spent a couple years working through total overhaul renovations on an on and off basis while renting those that weren't being renovated. While there were a few bumps in the road, I still think it was a great investment deal. Purchased for $95k and in its roach infested, poorly maintained status it was grossing $2k/mo. Now fully renovated, it grosses $3,300 for 2 studios and 2 1-br units. I had always planned to hold it because the return is so great but there's a few downsides: 

1. I hate managing tenants. They're needy, they never pay on time, the turn over is pretty high (but vacancy is low), and I'm too nice to enforce fees, etc. Admittedly I let them off too easy because I'd rather not deal with listening to peoples sob stories about why rent is late or they need out of their lease early. 

2. Due to a divorce, I was forced to take out a 401k loan in order to pay off 2 HELOCs totaling $30k that had been used for apartment renovations. I'm pretty conservative with my money and knowing the loans would have to be paid in full if something happened with my job makes me super uncomfortable. I wouldn't have done it if I'd had any other option. Its currently on a 5 year repayment plan. 

3. Another wrench in my plan came when I initially thought I'd do a cash out refi to buy my next rental after putting in all the sweat equity on this place. When I refinanced last spring to try and roll in renovation costs and see what I could get beyond that amount my appraisal came back SUPER low. Appraisal was done through the lender so maybe that was my first mistake. They basically said they couldn't find any comparables so they had to go with what was out there and they valued my property on a per unit basis alongside some 4-8 plexes with double the bedrooms that rent for 70% of what mine do (aka akin to the status of the condition of mine prior to renovations). 

So here I am 3 years after purchase, wanting to expand my portfolio but feeling stuck because I also want to snowball this 401k loan. I don't have the money for a down payment on another property and when I run the numbers I probably wouldn't for another year and a half. This place is in a transitional historic neighborhood. All the investors are coming in and flipping historic properties and the young professionals are going crazy for the cheaper than downtown rent. I think an investor who has more grit to manage tenants or a property management company would go nuts for this place. My gut says I can sell it for enough to pay off the mortgage and the 401k and walk with $150k (although I'm working with a realtor to verify I'm not being too lofty with my assessment). But if I sold it, I don't even know what I'd do with $150k. I want to "retire" (aka not be tied to my corporate job anymore) in 10 years. I need cashflow from my rentals for retirement. What I can't wrap my head around is if I need to suck it up with the current property, pay down the loan and wait a few years to buy my next property or if I'd be better off selling, paying off the debt and picking up 2-3 other properties in the $100-150k range. Or maybe I just need a different investment avenue that doesn't involve tenants at all since that doesn't really seem to be my thing... how can I snowball my hypothetical $150k into something bigger?