From what you’ve described, it sounds like you’re more focused on long-term appreciation and future benefits rather than immediate cash flow.

Portsmouth, known for its historic charm, offers higher prices but strong demand for both multifamily properties and short-term rentals, with premium rental rates for well-located properties.

Hard money and private investing are both ways to finance flips, but they work a little differently.Hard money loans are typically from companies or private lenders that specialize in short-term, high-interest loans.

You'll also need to show stable income for the past two years through W-2s or tax returns.Talk to 3-5 lenders to compare their rates, fees, and terms.

Prepayment penalties- usually 1-5 year terms.

A 1031 exchange will allow you to sell your building and use the proceeds to invest in a small multi family and/or medium term rentals.

I have 3 long term rentals, but this is my first time with commercial property. 

Refinancing: If the lender doesn’t approve, refinancing under the LLC might be required, but LLC loans typically come with stricter terms and higher rates.3.

Check out the Short-term and Vacation Rentals forum.

The terms may be more favorable, if you are just starting out a bank maybe nervous to do 3 at once, therefore their perceived risk will likely be reflected in less favorable terms.