KNOWING real estate (or delivering babies) is a requirement for an expert. 

As for the "seasoning", some lenders will require the property to be "stabilized" (perhaps 80%-90%+ occupied, depending on the lender) for 3 months, 6 months, etc. before they'll do a cash out refi.

The lender will require that you live in it for 12 months and then you can rent out all of the units after that and start the buying process using the same strategy all over again after that 12 month period.  

Multi-family properties many times provide a better return per square foot than single family, which would be to your advantage as well.As long as you're mindful of the reinvestment requirements and purchase at least as much as you sold and use all of the proceeds, you shouldn't have any issues with this strategy.

It is also important to consider the transactional fees associated with originating the HELOC, whether an appraisal is required etc.

I have focused my research on house hacking due to the lower upfront capital requirements with an FHA loan.

I thought this was simply the right thing to do and did not give a second thought to undergoing this process until after the repairs were completed.

@Marcus Stokes Starting your first fix-and-flip can be exciting but requires careful planning.

This isn't always the case, but in general, I've found Section 8 homes tend to require more frequent minor repairs.

So for me the decision was pretty straightforward, but it still required a lot of thought.It’s not easy out there these days folks, best of luck!