I too am based in Chicago.

Vice versa, if you are just starting out, you might want to be more conservative to tackle any unexpected expenses that arise.The 70% rule is an industry standard, but that doesn't mean you can't adjust it based on your desired ROI.

I'm totally looking for somebody that will help out with the paper work and keeping within the law; and also (And just as importantly) help finding the deals based upon my criteria.

If it was about buying properties, it would be called "collecting".Assuming a property that is good for both, one simple way (the best way) to see which is best is based on comparing the potential profit from a flip to how many years it would take for the potential cumulative CF to equal that potential profit. 

Many of these financial advisors make money based on the portfolio and/or trades made.

The amount is based on youngest age of the borrowers. 

And yes, RE prices have now dropped dramatically on local vacation rental homes.Your 5-6 bedroom home strategy makes sense and we are currently seeing the highest demand for that home size.

It is not in my nature to go out and give bad reviews, but I feel obligated to warn people about a group based in SoCal who sell rehabbed and rented properties in Alabama.

There may be some local business that would LOVE that property as-is, that just doesn't know about it.I'd start with some fliers, and walk down the street, drop one off at every existing business.

I’d also think about creating a sales position that is based on commission.