I found out an extra payment goes alot further on high interest rate.

I also provided several cashiers checks totaling $4000, which the agent claimed were for good faith but have not been returned.

The downsides can include high minimum investments ($50K+) and just learning how to vet syndicators, but you can knock out both by joining a real estate investment club.

If I let it run its course the system prices regular dates too high and it prices our peak season festival dates too low.

The reality is that a property properly renovated to a high level and eliminating deferred maintenance that is also managed at a very professional level, can and will outperform a marginally renovated property with marginally good management.

Your debt you are taking out does not incur any taxable event, so using that capital for your purposes is wise if you want to keep the asset the debt is held against, assuming your getting a better rate of return then if you didn't have the debt. 

I was going to go with "High net worth individuals (HNWIs) are those who have at least $1 million in easily convertible assets like cash, stocks, and bonds."

I would suggest you target a 20-30% annualized return on a flip considering the timing, funds invested, and return.

I'm analyzing existing properties while I research the development side - I would really like to develop, but it just depends where the best location and returns are going to be (but I love a clean slate).

Rental Comps for the zip code are high.