I think my odds are stacked against me on this one.

Once you establish your REA license, you'll find that depending on who you broker with, that brokerage may have rules that will restrict you in doing some of the things you would want to do as a REI.  

If you are buying a primary residence you don't fall into that category, so you won't have the same restrictions.  

HelloQuick scenario is I got an off market property large enough to subdivide square footage wise however the lot is odd shaped so when I split the lots to meet the minimum widths the one lot falls short approximately 800 square feet.

Not a statistician-- but unless you are having an economic downturn (or all work at the same place and it went under)--collusion sounds likely as the odds are against all tenants suddenly having a financial exigency at the exact same time.Word may have spread that nothing serious happened with late rent (no late fee?

I am trying to push a deal to her as the property is odd and not really appropriate for a traditional retail buyer since it would require significant rehabbing in order to work as a rental or owner occupancy. 

As to your second question, oddly enough it appears she worked a deal with the Sheriff's to become an informant for them to help them catch others whom might be trying to pull the same scam on other property owner's.

You can improve your odds by altering your approach.

I'm finding the hard part is more finding properties that are in a good location and also don't have restrictions on short term renters (either hoa or local regulations).I've reached out to owners with the same basic offer (increase rent, cover repairs up to a certain amount) and most people are hesitant to even discuss it, so i think it's a sheer numbers game and being ready to buy a property when one shows up that matches my criteria

It is very odd.