It blows my mind that people are willing to spend a good chunk of change on a piece of property that they will be tied to for, probably, years to come but they don’t want to spend a weekend and a few hundred bucks checking it out.

In my market here in the Chicago burbs, it is common for the owner to have to chip in a few hundred every month while they are living there. 

My understanding is that he use to have hundreds of units but down sized as he got older.

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.