I shot you a DM as there are most likely a few different options to consider.

For multifamily, target markets with strong rental demand, value-add opportunities, and creative financing options like seller financing or private capital.

North MS is a great option as well! 

I haven’t seen many value-add products, but there are solid options on the DSCR side.

Here are some financing options to consider:HELOC or Cash-Out Refi on Another Property – If you or your mom have equity elsewhere, this could be a more flexible and lower-interest option.Business Line of Credit – Since the property is in an LLC, you might qualify for a business LOC, which could cover construction costs.Private Money Lender – If you’re okay with 12-15% rates, a private lender could fund this as a short-term loan, especially if the guesthouse will generate strong income.Construction Loan – Some lenders offer short-term construction financing, which converts to a longer-term mortgage once completed.Seller/Partner Financing – Bringing in an investor or structuring a joint venture with someone willing to fund the build in exchange for a share of the income.Credit Card Stacking or Unsecured Business Loans – Riskier but could work if you need to bridge a gap until the unit starts cash flowing.Would love to hear more details—especially your timeline and expected rental income.

Should I get preapproved before searching to know my options?

Since you're looking to house hack your first multifamily in New London, CT, or Greater Boston, connecting with local investors and learning about financing options will be key.

Berkadia is #1 Freddie Mac Optigo, #3 Fannie Mae DUS, and #3 HUD/FHA multifamily lender in the country as of YE 2022, and my team originated ~$325,000,000 in agency loan volume last year.Lately I’ve noticed many of you asking about multifamily financing options, and thought this would be an opportunity to host an AMA regarding Freddie Mac and Fannie Mae agency multifamily financing, an area in which I specialize.

One option I'm pretty familiar with is land conservation easement/fee simple - though this is more of a strategy to help with all AGI rather than strictly capital gains.

Also, explore creative financing options that might balance your partner’s limited credit/cash flow without putting all the risk on you.If you're attorney can't clearly articulate this, maybe it's time to find a new one.