It is a huge pain in the ***.

HOAs can be a pain both with fee's and rules regarding rentals.

One thing to look out for is UBIT (Universal Business Income Tax)....Any Investment you make in your IRA that also has leverage attached to it will open you up to UBIT...this will be painful so should be avoided in most cases (unless the ROI is so good it justified incurring a tax inside a tax sheltered account).This doesn't come into play if your IRA is lending money but only if you are buying ownership in a property. 

A $10/month policy could have avoided all this pain and suffering.

It happens fairly often (no-shows) to all landlords so we feel your pain.

It also brings the pain/ punishment if they screw up.

That sucks but this is a fallen world filled with pain sorrow and trouble .

@Rik Shaw I've owned investment co-ops and while I did make money on them they are a pain.

I want to use profits for income first but I know taxes can be a pain (I'd like to avoid/minimize those as I have a lot of student debt I want to minimize before starting an official business).

Plumbing is one that is a pain to deal with, however it doesn't look like anything serious according to the plumber, all PVC throughout , besides some of the hookups are cast-iron leading to the PVC.