That said, I suspect it's a loser from an investment standpoint, because of the costs involved.

Both were customers, ran small business, and held money with the bank.

These two work very well together and have worked on several transactions together which is important for communication amongst all involved.

@Will Boller, in a quick click around on Interval International's website (https://www.intervalworld.com/web/my/home) a major exchange for timeshare properties, it seems like it is 50/50 from my small sample looking at properties in the northeast USA, with a handful allowing Sunday weekly check-ins too.Granted, this exchange is not an Airbnb, but it is all weekly stays in condos run, presumably, by large professional operators that have studied this business to maximize revenue.  

It is always more difficult to end business relationships with friends and family but you can't treat these working relationships any differently.

Keeping rates high could destroy capital intensive activities and businesses.

Might be best to list my business address but in reality I need all the mail/tax papers sent to me. 

I'm relatively new to the real estate investing business and wanted to start out house hacking.

I wanted to ask the community for any tips you might have on where to begin learning this business and possibly some guidance on what kind of work I could be seeking out as a student with no background in this industry.

I have 16 years of investing experience and have been involved in over 5K real estate transactions.