The fear of renting while out of town is common, but it's easy to overcome, especially when you have friends and a handyman.

Or, what’s something you don’t hear discussed often that could help me avoid common pitfalls?

Typically people think FHA because it's what's thought of as the least amount down which is commonly the goal when we all get started.

@Brian Dolbeare This is a "it depends" question for sure, but in most cases street parking is pretty common here.

I'm not sure I would get to cute trying to squeeze every time out of it now with a lease that might cause you issues in the future, but the scenario you describe is common and probably smart. 

I don't think the HOA can restrict what a tenant does within their own unit (the lease can), they can prevent activities in common areas.

@Kevin Waymire Asset management is something that is commonly an after thought.

Here's some online software options that you commonly see recommended on BiggerPockets.

This is a straightforward and common approach.However, make sure to document the change in the lease renewal or addendum, specifying the new security deposit amount.

Being above four units, fairly common for the accepted offer needed before showings.