I secure the property and does the rehab, and he is paid on the back-end once its occupied and refinanced.How does a deal like this work?

Dan, I appreciate your post and it helps with my decision of trying to figure out this method.

As such, in an effort to satisfy my own curiosity, is it ridiculous for me to consider cross-collateralizing two vehicles to secure a loan and get started with a house-hackable duplex or other small investment property?

If your local market has a shortage of open apartments, people may be applying to multiple places even if they aren't sure they want it, in an attempt to secure housing.

It is very difficult with all the different ideas, methods, and stuff on BP to not SQUIRREL!

@Paul Thompson ok, then if you are buying with cash and then seeking to refinance there is a proper method of doing this and still being able to refinance with Fannie/Freddie loans. 

@Brian Adzadi the 'house hack' method isn't an option for me unfortunately due to a few factors (beyond the terrible market for rentals where I live).

BRRR method basically.

Should I strictly just use zillow/real estate postings, or is there a better method that you would recommend?

I also was advised to talk to a lawyer about holding the closing company liable as their email servers are rarely as secure as they should be and are targeted as a result by scammers.