I am assuming you are getting the HELOC for the down payment and that you are going to get traditional debt for the rest of your purchase.A lot of people treat helocs like free cash and then get hurt when it is due. 

When I refinance into a traditional 30 year fixed, the bank will only loan 75% or 80% LTV ($120K or $150K).Long story less long, if you all were to find a $300K deal that you loved, how would you go about paying back the private money you received to acquire the property?

Traditional people from cultures that actually respect marriage.Met a bunch of them.

I purchased the property for $150,000 in Oct'2015 and spend the winter of that year renovating it from it's dungy 1950's look to a traditional/modern lake house.

Call it what you want, but this is not a transactional loan in any traditional sense and certainly not risk-free.

Rehab a property, then create a traditional mortgage to pull my cash back out for next project.  2)  Get home equity loan...rent out my house in San Jose, CA for a good amount of rent income...then use my loan to do a flip somewhere more affordable.  

That being said, it could make more sense to you to buy for low to moderate cash flow but strong appreciation, versus the other way around.If you want buy and hold rentals, I’m hoping your idea isn’t to tie up all your cash in ONE property, but rather to get your own traditional investment loan or creative financing from sellers.Another consideration is many speculate we could be nearing the top of a real estate market cycle, with a dip in home values expected when you could pick up some better deals.

@Joseph Blanchett, as military, traditional lenders will be tripping over themselves to lend you money assuming you have any type of credit history at all.

Wait for traditional financing. ( end of 2019 - would force me to rent too long )4.

Traditional homeowners may not like it.