Hi Benjamin, I’m in japan and doing real estate investing here for about 8 years in different styles besides my full time job.

Cowboy style.

Even with the discount, the investor will be a life style investor who wants to own in PR more than optimize return.  

It does sound like we have similar interests (and design styles), so we would love to connect!

But if it were the real check why would the company use a hand-written font and then somehow digitally sign it with messy cursive in the same exact ink style as the typed font?

I would pick a market area you like and start doing a bunch of deep dive deal analysis, but from a rental and not a life style standpoint.  

I work with a lot of MTR investors and what I am seeing frequently with multifamily acquisitions, particularly with new investors, is that they often test the property just like you're mentioning, as a way to dip their toes in the water and see what works in their area and for their personal style.

@Kyle CarterAsk about their communication style, does it fit with yours? 

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

One more thing, especially for people who don't meet my criteria, besides more deposit is required, I also do a interview with them, not interrogation style, more like a friendly conversation to figure out their situation.