He offered to buy me out so we agreed on a price.

Fortunately I work in the insurance industry so I generally knew what to watch out for.

It sounds like your cleaner is charging more no matter how many people stay, so I would recommend upping your nightly rate a few dollars to make up the $50. 

Ask about any unforeseen challenges that have come up (there always are, so not all challenges are a red flag), and overall let them know you're an involved LP who likes to be kept up to date on things

While many investors want to purchase properties that offer BOTH cash flow and appreciation potential, those properties are priced so as to provide a total return less than either  cash flow or appreciation types of properties.  

I’m also a dog lover and mom to a beautiful Yorkie boy who brings me so much joy.I’m a lifelong learner who loves reading, exploring new ideas, and being part of communities that bring out the best in me.

That said, there would be arguably no business purpose to bringing your family along with you, so even if you are spending the entire time searching for real estate.

Wow, thank you so much for this information.

My wife and I are still in the 'learning phase' as real estate investors, but we know for sure that in the next year (a) we will be converting our primary residence in to a rental, and (b) buying another house that will be our primary residence for 1-2 years so that we can qualify for an owner occupied mortgage.

So, then what?