I have some upcoming repairs needed that outweigh the Homestead Exemption and plan to make my primary home a long term rental in the next 7 years but the repairs can’t wait.  

Hi Anthony, what's your biggest priority - cashflow or long-term appreciation? 

But I think they may still beat SFR in terms of cash flow there. 

However, after accounting for long-term capital gains tax and other expenses, you would be left with $150k which is important to budget and account for.

I purchase my personal investments to maximize their equity and hold long term.

I am excited to get started investing in real estate in out of state Long Term Rentals.Outside of real estate, I enjoy spending time with my kids, as well as mountain biking and other outdoor adventure activities.Excited to learn and connect with you all!

I'm looking to finance the project long term in a way that is helps me create positive cashflow.

Since you are already familiar with house hacking, I would consider converting your current home into a rent-by-room or whatever it takes to keep it as a long-term rental, then look for another home you can hack.

I have found there to be a real shortage of long-term rentals in Ludlow and the surrounding area.  

The HELOC would act as en emergency way to tap into their equity if needed - as long as they don't spend it unwisely!