The property was leased for $2,150 per month.Refinance and Return on InvestmentAfter a stabilization period of 6 months, the property was refinanced to leverage the increased value created through renovations.

If My father and I use the heloc to fund the repairs; I'm concerned to have payments on a heloc as well as giving up all the cash flow for a period of time.

Further, Reg D 506 C offerings can accept new investors money right away, while other private placement exemptions require a 90 day waiting period for investments from investors with whom the sponsor did not have a prior relationship. 4.

It's working out ok other than some latent defects the seller hid from me and my inspector during my due diligence period.

Many people don't realize that you gain as much or more net worth through debt pay-down, and while it's less liquid than cash flow, over a 5-10 yr hold period it's considerable if you buy in the right areas with the right asset class.

I am curious though, in hindsight, how does an investment in STR in Hawaii in 2012 would compare with other markets over this period of time despite all the regulation headwinds?

Maybe you could extend the closings with some additional earnest money (even if you release it) and buy the time so you can simply do a regular 1031 exchange.  

They're looking for a stable market that is gobbling up houses just after a slow period so they can still get good deals on land before it gets hot and popular again.  

Most who make $500k don't have nearly enough dry powder on the sideline to scale a real estate business quickly enough without making huge personal sacrifices for an extended period of time.

Period, end of story.