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.

I’ve often seen this happen where initial approval is given, but debt-to-income issues arise once they discover you’re purchasing another property.

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

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

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.

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

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.

It’s a common practice and I’ve never had any opposition to this provision.If you don’t have an operating company, you could get into contract in your own name and then assign it.