They are in their 60s now and have adult kids , but just those two smallish buildings were able to create generational wealth.

As you are getting started in real estate investing, what are your favorite podcasts to listen to for information, entertainment... anything?

Maybe having an adult conversation with the man will help you make your final decision. 

I knew way too many people to party their way to a 6 year bachelor's degree in something they don't use, living with parents and still basically adult children.

@Thomas Burnett, not trying to burst Aaron's entertainment balloon, but as far as I can tell, you're not in anything yet, so do not need to get out of it, right?

I think I almost had a similar story...My locality took some cookie cutter landlord tenant regulations (from Seattle, I think) and was entertaining passing them in some sort of housing plan. 

The partiers were not residents, it turned out one adult tenant had been marketing "pool parties" to non-residents at $5 a head.We have a "no parties" clause in our rental agreement, and also do not allow residents to run businesses on the property. 

That's when the upper unit tenant called me, as he's never really had this problem before and really didn't think he needed to call me because they are all adults but felt it was a big enough issue and now he is thinking about not resigning the lease for next year.  

@Stephen KunenProviding substantial services to your hosts provide suggestions that you should report it as schedule C as opposed to schedule E.Substantial services include but not limited toConcierge, meals, housekeeping, cleaning, entertainment etc.A pro of reporting it on schedule C is that losses are deductible and not subject to passive activity rulesA con is that income will also be subject to self-employment taxes in addition to income taxes.

I was told by the district's planner that a residential facility which houses 3-5 Unrelated adults is permitted in all districts except Limited 1 Family.