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Seeking to connect with a Real Estate Investor/Contractor in South Shore, MA.

Build your network by joining local real estate investor meetups or online communities like BiggerPockets.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

I'm an agent and investor in Sacramento.

So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

He was very patient with us as first time real estate investors and went to bat for many different properties for us.

Commercial deals take longer and are all about relationships, so connecting with investors, brokers, and property owners is key.

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.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.