Now, if you were to buy properties that appreciate, I have no qualm about selling that property and upgrading to a property with more units and a better ROI.Out-of state rentals are okay when you have a good management company, but it is fairly difficult to get a management company that is really good and there are hundreds of reasons they are not good.

Encourage your child to apply for hundreds of scholarships and seek cheaper education, if the child needs a student loan he/she can get one but teach them a valuable lesson about money and debt and encourage them to avoid unnecessary student loan debt.  

There are hundreds of investors that will mentor you for something in return of value to them.  

There are probably hundreds of posts on here about someone's significant other not being on board with investing.

I’m not spending hundreds or thousands to put fancy landlord locks in all of my units.

Your best bet is a real estate agent with a verifiable proven track record of success with closing short sales ( and not 3 lol...tens - hundreds preferably).

I thought I was capable of making a couple hundred thousand dollars a year and that’s where I would land.

Assuming the ceiling damage does not include rafters/joists and is only a question of replacing drywall/tiles, that should only be a few hundred. 

You'll need a coherent approval policy, an application process, solid leasing documents, and a hundred other things you haven't even thought of.

May be handing off the property to a PM in the near future though as I am moving a couple hundred miles away and not sure that I wanna manage it on my own.