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

Even then you need a business license if you are collecting any kind of payment for it even if it is your place.  

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

@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.  

Business is about making good decisions.  

Keeping rates high could destroy capital intensive activities and businesses.

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

NFL, NHL, MLB), relocations, business travelers etc. 

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.

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