The existing homes are too small and would require a large expansion, at which point it would just be better to build new. 

A triplex or quadplex could provide more units for rental income, but obviously will require more financing, so having your financials and pre-approval lined up early is key.Since you’re already looking to network, attending local real estate meetups is a great idea—you can also connect with seasoned investors or agents specializing in Long Island properties who can offer advice specific to the area. 

Once you read the explanation below, you will understand how REALLY bad things can be if you don't get the letters but go through with the purchase.First, the owner/seller should have a clause in the lease requiring tenants to sign (or object to in writing) tenant estoppel letters if presented to them.

@Stephen Hood your idea is solid and shows good potential, but here are a few things to consider:Private Lender Terms: Ensure the lender agrees to the 1% origination fee and $2K monthly payments—some may require a higher interest rate or balloon payment at the end.Timeline for Sale: Factor in potential delays with selling your current property or completing renovations on the new one, as these could impact your refinance timeline.Refinance Feasibility: Confirm with lenders that refinancing at $500K is realistic, especially after recent rate increases and appraisal expectations.Exit Plan: Have a backup plan in case the market shifts or repairs take longer than expected, such as extending the private loan or bridging with a HELOC.If you can lock in favorable private loan terms and stay realistic about costs and timelines, this could work well.

I cannot use Airbnb since it turns out the conversion is unpermitted and my city requires STR registration.

It's lower leverage, higher pricing requiring a solid exit and good credentials. 

So my solution was nearly zero work, almost no experience required, and an improvement on their current zero income solution.

Now my situation may required less, but the company who did my crawl space did an excellent job. 

However, if you or your spouse can meet the Real Estate Professional Status (REPS) requirements by working over your w2 hours in real estate and materially participating, the rental losses could offset your active income.

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.