Please read this:https://www.biggerpockets.com/forums/51/topics/1088325-expla... 

I think a return on invested equity analysis outlining a few scenarios with my models would answer your questions. 

I have started my research on management companies in the area and will take your suggestions and learn more on this topic!

FTR, I'm doing exactly what you outlined.

They have have done a great job outlining all the possible things that can go wrong and what  can go right.  

I rest my case.And here is my older post on finding good CPAs:https://www.biggerpockets.com/forums/51/topics/1222774-expla...

these investors were all chasing easy OOS cash flow:https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1160450-run-i...https://www.biggerpockets.com/forums/48/topics/1137397-balti...https://www.biggerpockets.com/forums/52/topics/1010977-12-00...if you're serious on investing in an OOS market i'd pick one, get to know it, go to it in person, and build a team, and then determine what would you need to do to get a good return in that market. 

They are much less restrictive than other municipalities in South Florida that are actively trying to reduce the number of STRs.Let me know if you'd like to talk further on the topic! 

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.