Hello @Jonathan Studdard
Thank you for bringing up this topic as I too am in a similar situation. I've got limited experience in REI but luckily purchased a family member's condo in 2012 in Jersey City (240k). I'm now working with a realtor I found on BP to sell it as there is no cash flow and I don't think the unit will appreciate much further. I think it should sell for around $400k (I have 170k left on the mortgage). I plan on using another BP member to conduct a 1031 exchange to reinvest in new rentals but, like you, keep going back and forth over putting the money towards a small/medium size apartment complex or buying 2-3 SFR. I truly wish I had the answer for us both!
Since I have 1 other SFR in my "portfolio" I know that marketplace better while I have no experience with regards to multi-unit apartments in investment worthy cities. Having more doors is definitely enticing and seems to be the way many other's have growth their wealth, but without a mentor and learning solely from the interwebs, I have been hesitant about going big.
I know you're probably weighing pros and cons in your mind daily, as I am, but here's to hoping the BP community can steer us in the right direction so in a few years we can be posting our process/results for the next folks! Hang in there, message me if you want to keep tabs on each other's progress or musings.
Best,
Steve