Flipping can be profitable if done right, but it can be time-consuming which may not be ideal if you have a busy day job. 

Sounds like you have the book smarts, which is important to make sure you can turn a profit. 

How far does joining a community only to profit off of others take you?

Your profit on deal #1 is $25k so you would pay taxes on that.

Become an expert in one location.There are thousands and thousands of real estate investors in Canada, profiting from their rentals.

Yes, I live in Boquete Panama and I own a small organic coffee farm so I know that business too. 

I would like to JV with an experienced investor for a share of my profit...

C-Corps usually aren't a preferred structure for real estate.I know that with a self directed IRA all of the income has to come back to the IRA - read another way - you can't take the profits from your investments and access them today (so no passive income that you can utilize in the near term).  

I won't make any profit on it, but he's paying the bills and our hope is that he will buy it from me in 1-2 years or we'll keep it as a rental and he'll buy something else.

Hi @Kent Kettell, assuming you're running the numbers on your end, any loan offer that enables you to acquire the asset given your level of cash reserves and reach your target ROI at the expected project duration, net of financing costs.If you don't already have a useful calculator to assess cost and profitability associated with fix & flip projects I'm happy to share a copy of ours!