@Amanda G., thanks for the reply.
No matter what, I want to pay off the HELOC. It will free up $600/month of cash flow and then I'll have the $125k available to me any time I want to jump on an investment property.
I'd also like to pay off the loan from my retirement account, since that puts me one step closer to my goal of quitting eventually. If I quit without having paid it off, I either have to come up with the money or pay a huge tax penalty. And since it is my retirement account, I get that money back eventually with interest.
Eliminating those two payments will roughly offset the loss of income from the rental property, and I'll have a chunk to reinvest in a 1031 plus access to the HELOC as needed.
I am fine with putting in more effort for a few years if it gets me to my goals. I'm already working a ton (day job, realtor, landlord, commissioned artist), so I can just reallocate how much time I devote to each of my side hustles.
If Boston weren't such an insane market, I would try to find another undervalued SFH or small multi and either BRRRR or fix and flip. But it's impossible to do anything here. In a perfect world, I'd find some large commercial space and hack it by putting in art studios to rent to all my creative friends, but that kind of space is also unavailable at prices that make sense.
I want more equity gain and income than I'm likely to get from syndication deals or notes, so I think this likely puts me back into more active roles like BRRRR or fix and flip, but in faraway markets. Those make me nervous because finding and managing great people is hard enough when you're local, but it seems it can be done if I can figure out a better system and I pick the right metro. I'd also be open to storage units, boat or RV storage, etc., pretty much anywhere.
My wife is starting to get impatient about the condition of the exterior of our personal residence, so I may tend towards doing some quick flips and pulling some of the profits out for that (it's a 2-family, so I can at least write off part of the work).
I guess that leaves me narrowing down to BRRRR, flips, or storage units somewhere far enough away from Boston as to still be profitable. Which then means I need to figure out what metro to invest in and start building a team there so I can be ready to jump in a couple of months when the house is sold.
As to what I enjoy, I really like identifying properties and doing deal analysis and making creative offers to get deals done. I don't mind the rehab process although it can get a bit stressful. I don't love being a landlord, but I do like the cashflow. I don't really have a preference for SFH vs multis. I am intrigued by commercial/warehouse, storage, and similar deals but I am still very much on the learning curve about how to structure those deals to make a decent profit.