Please help me get unstuck from the Analysis Paralysis! Thanks :)

[Kyle Calabria]

Hey all! New to the BP community and I’m hoping for some help getting unstuck from my analysis paralysis. Thank you in advance!

TLDR:
$500k to invest in multi (3-12 units), based in Boston, trying to decide between Sunbelt or within a 2hr drive (likely Hartford, CT or Worcester, MA), basic renovation skills, currently operating MTR duplex house hack, on break from career in tech that may return to, investing goal 70% cash flow, 30% appreciation.

Full context:
I'm based in the Boston area where the entry price point is high. I own a single family home in Medford, MA and I converted the basement into an ADU that I rent to traveling nurses on a 3 month contract basis. The income from the ADU covers the mortgage payment ~$2,500. I did a lot of the renovation work with my father who's an engineer and learned much of the basics from him (demolition, framing, insulation, basic electrical and plumbing, design, flooring, etc.). I did sub out a lot of the work as well (drywall, vinyl flooring, bathroom tile, countertops, paint).

I have a career in data engineering/analytics in tech but recently decided to take a break from my W2 career to focus on building out a real estate portfolio. My plan will be to return to my career to pay off the real estate I purchase and get up and running during this break. I don’t have a set duration of the break. My investment goal on the cashflow to appreciation continuum is 70% cash-flow to 30% appreciation. I have saved up $500k currently sitting in a high yield savings account that I'm eager to deploy.

I’m open to value-add projects for light to medium renovations but also open to turn-key (particularly if OOS). My search aided heavily by Claude first took me to the Sunbelt. I booked a flight to Atlanta and was planning to drive (Northern AL, Chattanooga, Knoxville, and Greenville) but the flight was cancelled due to the big snow storm. I didn’t rebook because my latest research/thinking was pushing me closer to home for my second deal. I toured an 8 unit in the South side of Hartford, CT (2 hour drive for me) and drove around the town getting a feel for it and driving by on market 6–12 units. My impression of the town was that it has significant disparities of wealth and that the rough areas were really struggling. I next toured two 4 families in Worcester which is only an hour drive and seemed to be more on the up and up. After both days I felt like it was a lot of driving and had me questioning whether i’d be better off just picking the absolute best market in the country for my goals (back to the Sunbelt likely or possibly midwest) and just managing it fully remotely. Regarding property type.. I want to balance concentration risk with economies of scale. I’m on the fence between 4 units with residential financing or 6-12 units commercial. Which unit size is market dependent.

I’ve done a lot of research at this point. Underwritten numerous properties. Listened to many hours of real estate investing podcasts. And at this point I feel like I need to give myself a decision timeline and pull the trigger. Any help would be much appreciated. Thanks!

[Dan H.]

Some thoughts

- fear can be good.  It can keep you from making mistakes.

- your first investment seems good enough I question have you considered repeating it.  Many investors would be ecstatic with their basement unit paying the mortgage payment   

- financing is a lot easier and with better terms if you have stable income such as a w2.

- local is not so you can actively manage it if you do not desire.    Local can be for if/when the $hit hits the fan.   It can also be for the local expertise and contacts.   Long ago we had a duplex in gulf Shores Alabama.  In back to back years it got hit by hurricanes.  It was so Déjà vu.  Including the contractors promising to work on our property and yet make no progress.   We went 2/3 of the way across the country to hold the contractors accountable and make sure they were working on their commitments.   At the progress they were making prior to going there, they would never complete the work.

- keep educating, consider finding a mentor, attend local RE meetings ups.

good luck