I would then have to deal with finding tenants, property maintenance issues, etc (or pay someone to do this), which is more than I really want to do right now. At that point I would be closer to a full time landlord, not a full-time software engineer who enjoys working on houses on the side!

A coworker found a company that handles most of it, and they call when they're tasked with fixing something, he then figures out if he wants to pay them to fix it or what have you, or if he just wants to do it himself. He says it's basically paying for his rent. Of course it's all about researching the companies. Worse case you sell off the house. Totally worth looking into though.

Run the numbers and compare in your next sale. As a rule of thumb if you can get 1% of the sale price per month in rent you’re doing awesome.

And a good property manager should take away 95% of the hassle.

You're saying that if the house sold for $500,000, you should keep it if you can rent it for $5,000 / month or more?

I've heard of 5% of 1/12th of the projected sale price, which seems more realistic.

Yes $5000/month would make that a great property. Look up the one percent rule.

There are lots of other things to consider but it’s a great quick rule of thumb.

Being a landlord has a totally different skillset...

The answer to this is usually complicated.