I typically don't comment on other's businesses unless I know from personal experience.

I personally would not invest in detroit as historically its not a appreciating market and for cash flow and I invest primarily for appreciation - I go off the location location location mantra. 

Our short-term residential investment property loans are typically 60-80% LTV and all are personally guaranteed by the borrower(s) -- we pull credit, background and PFS on each guarantor, verify experience, verify liquidity, underwrite the property, neighborhood and zip code.

@Richard Rafferty, given the relatively small nature you are looking to take on with your first syndication, personally, I would find it hard justify the typically 20-30k+ for a paid mentor. 

I've know him personally for years, had the opportunity to consult with him on both sides of the business and have to say he's the real deal. 

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

This is so I know if I should keep the person I currently have.

Be that person who set's up some STR's there, runs em there, and really caters it to the US "bucket list" tourist. 

This is basically a math problem that will depend on both you personal finances & also how much of this is an investment vs you want a nice house to live in4.

Tell me - someone selling their home to your son, Subject-To - is this a person who has made good life choices?