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.

Sale Price compared to List Price has quickly regulated up to no noticeable difference between what a property is listed for and eventually selling for on average.

I work in restaurants operations management and would eventually like to get out of the industry. 

Additionally, can you eventually do a BRRRR refinance with a traditional mortgage?