That property is now a reliable source of rental income and a constant reminder that success starts with taking action, learning on the fly, and embracing challenges head-on.

I would still use quickbooks to track the finances in that account snd all rental associated finances (we use it to track are personal finances also). by the way it is worth the cost of paying someone good with quickbooks to do the initial setup.  

Unrelated persons ordinances are common. 

Each week, I personally analyze the MLS, leveraging my deep knowledge of South Florida’s short-term rental market.

So that helped.I personally wanted to be more conservative as I pretty much reach “the number” that I needed (note that what “I needed” is different from what “I wanted” or what I was expecting by default.)

We try to work with the same subcontractors as much as we can - it's the only way to establish a long term relationship. 

Out of all the tools I would personally suggest Pricelabs for sure.

I’ve personally found that specialized property perks can create stable, long-term renters.

This reminds me of a police officer  pulling somebody over without reasonable cause and asking to search their vehicle and if the person does not consent, they’re saying you must have something to hide.

Trust me, I have been there.I suggest you try to House hack in cities that you are already familiar with and have some connection with.Hire a great investor agent in that market and ask them all your questions and concerns.That I believe is the best way to get personalized advice tailored to your goals and lifestyle.You giving out Cleeveland and Toledo on your post will only attract biased opinions and advise.Only you know what you truly like, want, and can deal with.As Nicolas said, read this post and comments and hope that gives you a new perspective. https://www.biggerpockets.com/forums/12/topics/1215726-break...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1137397-balti...Goodluck and keep us posted.