This is from some professional storm chasers.

I like having everything based in the cloud.

You probably do not want that bad credit cloud over your head for several years if you do a short sale or foreclosure.Good luck, you'll get a lot of good advice on here!

It connects to your Dropbox account, so everything is taken care of on the cloud.

An attorney can draft a profits sharing arrangement and some instruments to cloud title.

So that's good and you have gross rental income of $9,000 per yearBoth ways can be rewarding and a as Brian Hancock artfully expressed, "a number of things may happen", which could cloud-up your returns (and your sanity too!

And, it's in the cloud so if your computer crashes you don't lose it.

It requires much more to manage 25 units than 5 units.Consider that Investor A with few resources and knowledge who owns one property could have as much reason to hire a property manager as Investor B with a full time job and little patience who owns 10 properties.On the other hand, Investor A with lots of skills who owns one property could have just as little need to hire a property manager as Investor B with lots of time and motivation who owns 10 properties.Bottom line is that yes, most owners do care more about their investment properties, but they shouldn't let that cloud their judgement if having someone else manage them is a more beneficial option. 

There is this constant cloud over me that I had better be producing more that I cost this company.

Sometimes we let family cloud our judgment in a situation like this.