What are the biggest pain points in renting?

Painful lesson but you paid it forward by sharing it with us.

'out of state' absentee owners, its just a variance in terms of levels of pain. 

This cannot involve origination aspects, but can involve structure, compliance, risk analysis, administration and management aspects for the lender.

It's kind of a pain to setup IIRC, and everyone is on craigslist anyway. 

Ever since I told the old property management company that I wouldn't be retaining their services they've become a pain in the butt.  

I have several QB files I work with during the day, closing-opening-closing-opening ... is a pain. 

Our privacy laws make the gathering and marketing of such lists {next to} impossible.4) The lender incurs both a loss of revenue (interest income) & capital (principal) in addition to realising legal fees (attorneys and court applications); appraisal fees {an appraisal is required when applying to the court}; administrative fees, etc.  

If hte HOA is the RSF and the Art Jury is the review committee then I feel your pain.  

Essentially anyone can be an administrator, and their main function is to perform administrative functions only.