Hi All - I am looking for perspectives on my options that might help me decide my next steps. Here's the story:

I own 1/2 of a duplex that is my family's home, where I raised my boys for the past 20 years. The plan is to market it as a long-term or mid-term rental. It's in a small working-class, old mill/industrial city in RI.

My bf owns a single-family home in a nearby suburban/rural/farming community. His property is gorgeous and is in a rural, mature neighborhood. The house was built in the 1920s as a hunting cabin that has been added onto over time. It's like a bunch of boxes with no real flow, with multiple floor levels, and is awkward at best. We've met with a builder who suggested it's more likely a tear-down & rebuild than a rehab candidate.

I unexpectedly lost my job in early October. I've been planning to invest in RE for financial independence, and now is the time. 

Here are my questions -

We've been round and round on our options and I'm really hoping someone here at BP can share advice and/or considerations he and I haven't already discussed.

- Do we rent my house and live on the cheap at my BFs? We'd look for a 2 or 3 family in the spring and sell his house as is.

- Do we live in my house, blow up and rebuild his house and sell it? Then we'd look for a 2 or 3 family to live in and rent my house.

- Do we sell both properties now and find a 2 or 3-family to live in?

Ultimately we're looking to replace my income and my BFs w2 income with real estate investments making up a significant portion of this nut.

I think it's also important to tell you that we're both in our early 50s. My retirement income is about 1/3 of what it should be. BF is in better shape, though not where either of us would like to be.

Some of the numbers:

ME

- I have a $115k~ mortgage balance.

- PITI, sewer/water taxes = $842.00/month

- 1,008 sq. feet + 249 sq. feet on lower-level. 2 beds, 1.5 baths, fully finished lower, fenced yard, 4-car off-street parking, dead-end street, 15 minutes from route 495 to Boston, 15 minutes into Providence.

- Electric heat. (tenant to pay)

- I had a property manager come out to the house who estimates the monthly rent at $1,500 - $1,700 (without advertising it, they'll share it with the "network of tenants" they've developed over time). I believe the property is more likely to rent for $2,000~/month. I've researched rental rates in the area and because it's a house with 3 complete levels of living and a private yard, generous off-street parking, and so on, I think it will rent higher than the average rents for apartments in the area.

BF

- No mortgage balance, paid $240k 15 years ago. Just paid off.

- Monthly expenses (taxes & insurances) = $492.00/month

- The house needs a minimum of $100k in upgrades, though more likely as I said above it is best as a tear-down and rebuild, likely $350k to achieve.

- A real estate agent I worked with recently to sell my parent's home did a CMA suggesting his sell price would likely be $279k~. That was back in April. She also said the house is detracting from the overall value and he has to expect less than average for this community, which according to Zillow is $479k~.

Please let me know if there's anything else I can share to help you weigh in. I appreciate your time and look forward to reading your comments!