However, at a recent meet up I was advised that it didn't matter too much; other things like finding deals and making offers are more important.

@Michael John what you should consider is “can I turn $300k around into a more profitable property that will generate more than $2500/month”300k allows you to put 20% down on a $1.5M property.

Here's a statement you will likely find on every credit/criminal background check:You are hereby advised that all information in the report is confidential and may not be disclosed by you to any person other than Applicant, and then, only in accordance with the Fair Credit Reporting Act (FCRA).Just because the Landlord hires someone as the agent doesn't change anything.

I was on the panel for this publication which can give you some great insights - https://www.nap.edu/catalog/24863/generating-revenue-from-commercial-development-on-or-adjacent-to-airports   Also, see reports 114 (Thru the fence ops) and report 47 (Leasing airport property) available on the same site. 

@Terry Lao, thanks for the great advise as always!

I would advise her on investing into a mutual fund that could earn 8-10% annually on her $100K, but otherwise, she can just use it as needed from checking account.

Running the numbers on STRs in Chicago, it seems like there is an opportunity to generate strong cashflow with minimal upfront investment by using this strategy, but I'm curious if anyone has on-the-ground experience with this type of model.  

Sounds like good advise.  

I learned how to run FB ads for some entrepreneurial ventures, one of which includes generating leads my own cash deals for BRRRR or flips.  

As I'm sure you know, there's virtually no value in the MHs themselves, but a good deal of value in the cash flow they can generate.