I am heavily leaning towards taking the job out in SD, I know that in order to succeed in my REI ventures(and many other aspects of life in general), I need to repair my credit and have a stable income.

Most major Canadian markets are heavily over-priced. 

Through my education about real estate I would love to learn a little bit more about the deal.CONSIDERATIONS: Things I would heavily consider is how you will get the people in to rent the property, being away for so long I hope you have built property management into the expenses equation as BP always points out.

If you want 1% rule on NOI (a minimum standard for a good deal in STR), then you’ll need 1.67% gross (1/.6).I know @Josh Messinger is seeing this in the Poconos as this is a market I invest in heavily, and I’m sure most of those Tampa rentals mentioned are in a similar boat.STR is my sole focus, always ready to chat STR if you reach out!

I donate pretty heavily to charity, but my business is not a charity.

One thing I am unsure of is this, are we supposed to care heavily about the 1% rule in a Lease Purchase sandwich agreement? 

Based on the information you've provided, I would recommend against you taking on the additional debt and putting yourself into a heavily leveraged, high-risk deal.

I funded WL heavily when I was working offshore and needed somewhere to put my money.

Again, you may want to be heavily involved early on to build your track record. 

McDonald's is heavily reliant on systems and processes, and even so, your experience (and Yelp reviews) of each one can be vastly different because it matters who the person is you're interacting with in front of you.