Or put the 88k in, refi out of the HML which requires you to come out of pocket quite a bit of money as well, and hold it long term which on paper may eventually make you whole.

I think doing this in the next few months would be really good because eventually once the rates come down I think I would gain some equity from the appreciation and then I could refinance and pull some money out and throw it in another deal?

@Josh Rodriguez, every property wears out eventually.  

This would allow you to eventually plan strategically to move into the new house and convert your current primary into an investment property... to then 1031 into your next project(s). 

I know eventually I might catch someone on a bad day.

You will eventually run into someone like @Michael S. talked about. 

Keep in mind HELOCs are interest only payments, adjustable rates, and will eventually turn into a fully amortized loan (usually after 3-10 years).Cash Out Refinances are great when you need the cash for long term needs or consolidating debt.

We are primarily looking for properties around the Buffalo and Rochester areas, and eventually venture out of state and tap into different markets.

Even if it does split the weekend, it usually fills in eventually, at least with my listing. 

Ideally, I’d love to house hack again for a year, then purchase a single family after a year to eventually sell or rent out.