Advice on Selling vs Holding and Renting

[Seth Martin]

Hoping for some advice from those that have been there before. 

So I'm trying to weigh selling my rental vs keeping and renting out through a management company. 

I am an out of state investor. I bought a townhome in the Charlottesville, VA area in 2019 where I was going to school. Lived there and rented half out to a roommate until 2023. I then moved out of state, and I've been renting it to a friend for the past year. However, he's moving out in October of 2024.

I initially bought the property for around $215k, but it's now worth ~$350k with about $165k left on the 30-yr mortgage that is at 2.85%.. I could rent it out for around $2200/mo. Escrow payments are around $1100/mo and HOA is ~$200/mo. After crunching the numbers I'd be cash flowing around $600-700/month if I hire a full service manager (and this is without accounting for any repairs, which it does need). Orrr I could sell it and get about $150-160k in cash to invest in in stocks or in a larger property closer to my current residence. The traditional ROI S&P500 for that amount of money would be fairly similar after accounting for everything. Just not sure if the headache and stress of owning a property out of state is worth the potential upside.

Any advice on what someone would do or has done in a similar situation?