I am often contacted by BP folks who have invested in real estate who wound up somehow on "a cruise they didn't sign up for."

I'm in Hades.Actually I’m on a cruise to Mexico at the moment.

I was cruising along quietly all year until August, when:- I went to have septic tank pumped at one house only to find it was falling apart.

Money wasn't an issue growing up and I got chances to cruise and see the country in ways that most kids didn't so I am hopeful that I will have enough properties one day to help fund vacations for my kids and maybe even a few of their friends! 

There will also be two Airbnb apartments upstairs which will be catering to tourists coming in for event downtown as well as cruise traffic.

live full time on a cruise ship, traveling around the world2. 

At that point I want to enjoy long walks, cruises with my wife, road trips, and dabbling with the periodic flip or property rehab.

It doesn't sound like a good cruise to me.

You can cruise some of the sites online that list MF properties and possibly find a diamond in the rough.

.- If I decide to flip towards holding notes I'm also going to need to properly finance my retirement accounts to "cruise control FI" explained in ChooseFI Episode 39.