Increase earnings, reduce expenses, save up, and invest.

Your expenses are not a reason to increase rent!

Run the calculations on the expense of doing a refi at a slightly reduced rate vs. keeping the current loan for whatever period of time you think you will hold this house.

If you’re considering leveraging hard money lending (HML) for this flip, it could be a strong alternative to traditional financing—especially since HML is quicker to secure and designed for investors aiming to flip properties fast.With HML, you’re typically looking at covering a significant portion of both purchase price and rehab costs, which keeps more of your cash free for other expenses or emergencies.

Your primary home doesn't produce cash flow and is a pure expense.

They're not stuck as in "there are no other options", they're stuck as in "there are cheaper, crappier options but we'd have to pack up our entire lives and deal with the other expenses/headaches that come with moving so I guess we might as well just suffer with the increase". 

Insurance is just an expense to factor into your underwriting just like property taxes.

Using avantstay for a rental management company caused me to LOSE an average of $6711 per month as they were not able to provide enough rental income to pay the mortgages or operating expenses on the two vacation market houses.

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

In MA, you can usually get insured with Fair Plan with certain pets, but it is VERY expensive.