A well-rounded property owner should have minimal issue managing their own assets IF the systems are set up properly.

And I'm sorry if this isn't posted in the proper place, I'm new here and still trying to figure everything out.Thanks so much for the help!

I'm not even sure what needs to be repaired here, but I would start with making sure all connections are fitted properly and not leaking.

Even that tub surround you wanted installed, often the stud placement isn’t adequate for a proper install and  requires $10 in materials that’s may result in several hours of work to get a quality install.More to the point, if the guy does quality work for you and you have no complaints about the end result, pay the man.  

I have not resorted to a letter, always get the cosigner's phone contact and do a CC and BG check on them or you are not screening properly.

On the other hand, I have that fear in the back of my mind that something will go wrong and I won't have the experience to properly handle it. 

You can't go wrong with buy and hold in any market conditions as long as it cash flows and you do proper tenant screening when filling the units. 

Some people are just not cut out for properly screening and managing tenants. 

No 401k and IRA funds are just way easier to keep track of when invested in stocks, not to mention if you are doing RE properly you should have a minimal tax burden, so why would you use tax advantaged money to invest in it, assuming you want a diversified portfolio.

That way, they have first hand knowledge of what needs to be done to properly manage their investments before putting it in the hands of a third party.