I feel like these are my only options:- House Hack: Would I still need to pay the 6% tax rate if I'm getting rental property insurance?

If the condition is similar to the market average but your rent is severely under market rate then I take an average between the current rent and the market rent and send them the following message 2 months before their lease is up (assuming you aren't in a rent control market),Dear Tenant,Some nice words and remind them that their lease is up within 2 months, please select the following options about their new lease, also mention that you are doing the best you can to maintain the rent as low as possible but with inflation, insurance and property taxes increasing, you have to raise the rent to keep up with the rising expenses. 1.

Your other option is to test it out and see if you can make it work. 

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.

Have you looked into property management options or run numbers factoring in potential vacancies and maintenance?

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.

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

Hi - if I am thinking about offering buyer with seller financing, what are my options for mortgage servicing?

North MS is a great option as well! 

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.