Be safe out there and be careful what type of advice you offer your clients. 

You know the answer.Just be a good landlord - provide a nice, clean and safe place for people to live and charge accordingly.

Decided to play it safe as it was my first deal and had to overcome the fear.

It serves many benefits for both buyers and sellers and if a law had been passed long ago that all such private transactions were required to be serviced through a thrid party, we would not have as much regulation addressing the issues we have today, specifically, the individual investors under the SAFE Act!

Or push through working another 4-5 years to make sure you were "safe"?

I really see Columbus Ohio as an extremely safe bet for the next 10-20 years.

With an HOA fee of $275mnth thrown on top, which is ROI for that as we get everything exterior covered 100% including lawn, snow, private dog park, hazard insurance, private playground etc.. 

Even if you have good folks on the ground to help you out, you are going to be making trips to take care of things that those people are unlikely to do, not the least of which is risk management:  Making sure your property is safe for guests, inside and out.  

And that get's even more confirmed when you look at home prices long term, like since WW2.It's like: I don't know if we are going to have snow for Christmas, or how much snow exactly it will be, but it's Wisconsin and so it's pretty safe to predict (even though maybe not 100%) we are going to have snow at some point next winter and the total accumulation is going to be probably around 30-50 inches.My operating assumption is that home prices are going to double (again) over the next ten years, just like the did over the last 10.

I did a lot of research, long term that’s a safe assumption.