They investigate your books, accident claims, accident logs, accident practices, if you are going to do roof - they might need an OSHA certificate, etc.

I have been investigating the possibility of short term vacation rental properties in Ontario.

I'll continue my investigation into the smaller commercial properties and I'll try to lean on some family members who have some experience in this class of REI.

I recently investigated Booking.com and to my dismay they are even more expensive, though I'm giving them a try and so far, NOT so good.  

And it will be good training; you may want to investigate developing/redeveloping other property in the future.

My husband and I are starting to purchase more properties in the Charleston area, and while we will manage them ourselves, I still want to investigate additional options just in case.

I am not sure about yours so I would recommend investigating that further.The legality of it aside you are not going to have any luck finding agents who would be willing to work with you.

Some people are telling me to just buy with 5% down as owner occupant and just rent out the units anyways, since is my first property the bank wont investigate as long as payments are made on time.

Even if you have a perfectly legitimate reason (bad payment history, property being sold, owner letting a child live there, etc.) you still have to deal with the complaint process and investigation, and the possibility of other charges being made against you if other things come to light.

There just isn't any "big money" investigating the returns for real estate investments in Pueblo that would push the returns down to the risk/return efficient frontier.