Characterizing an LLC as equivalent to fee simple real estate can only be done with single member, single asset LLCs.However, in a drop and swap scenario, the LLC would dissolve and the assets be deeded to the individual members. 

You might also be able to employ a short term rental strategy to increase cashflow-- sporting events, conferences, homecomings, graduation, etc. always attract people to the area.Ask around and try to find people who are investing in Amherst/Northampton and connect with agents in the area to see what's working.

So, I came accross a short term rental market analysis report for the city of Fresno, and found a really interesting chart representing the seasonality of the short term rentals. 

Because his job is 1 year term-renewable, we leased a 1000 SF 1st floor 2 BR 2 BA condo for $1500 before we knew I was pregnant.

We are experiencing a decline in rental prices both for annual and short-term rentals.

Option 1:Pros:Simplicity: You avoid the potential complications of alerting the lender.Maintains Low-Interest Rate: Since your loan is at 3%, you continue benefiting from this favorable rate.Avoids Immediate Full Payment: You won’t be forced to come up with $45k immediately.Cons:Risk of Detection: If the lender identifies the payments coming from an LLC, they might call the loan due.Potential Consequences: If the lender enforces the due on sale clause, you might be forced to pay the remaining loan balance quickly.Option 2:Pros:Transparency: Being upfront might build trust with the lender.Possible Flexibility: Given your solid payment history, the lender might agree to the arrangement.Legal Compliance: You avoid any potential issues with violating the terms of your mortgage agreement.Cons:Risk of Loan Acceleration: The lender could still decide to call the loan due, forcing you to pay the remaining balance.Potential for Higher Payments: If forced to refinance, you might end up with a higher interest rate.Given the pros and cons of each option, but a cautious approach might be best:Consult a Real Estate Attorney: This can give you a clear understanding of your legal standing and potential risks.Evaluate the Importance of the 3% Rate: Weigh the benefits of keeping your low-interest rate against the risks of potentially having to pay off the loan early.Consider a Gradual Transition: This method allows you to continue benefiting from the low-interest rate while reducing the risk of triggering the due on sale clause.

I found that most of recommendations to buy a duplex emphasis on positive cashflow or match with simple 1% rule to start with.

I would use the long term strategy as the exit strategy since str laws are stricter. 

But we do want the option to use it as a short term rental in the future.Do I need to go the ADU route - separate address, utilities, etc?

Something I am currently interested as well.4BR/3BA SFH (possibly smaller if the numbers make sense)Between Kissimmee & Lake Nona area (not something like pine hills)30-45 minutes to Disney & tourist areaNo HOA or low HOAMust allow a short term rental (open to long term rental if the numbers make sense)Last property I was interested in, I found out that it only allowed 7 month leases for rentals.