To help get better answers, include specifically, principal balance on loan 1, principal balance on loan 2, interest rate on loan 1, interest rate on loan 2, initial and remaining term on loan 1, initial and remaining on loan 2, interest rate on contemplated new loans 3,4,5, closing costs for loans 3,4,5, annual taxes and insurance, household income, available cash you could bring to table, any other constraints that you have.
From what you’ve posted above, and a bunch of guesses I could make, you should keep loan 1 and accelerate payoff of loan 2. With over $350K/yr in income, $3K/mo in mortgage PITI should be almost unnoticeable (and therefore no reason to pay $40K to buy $250/mo cashflow).
I’m more than happy to go as deep as you want in analyzing this and help you make the best decision for your household.