They think every other deal they come across is priced $50,000 below market value2.

ITs a known marketing method and it works obviously. 

However, I am intrigued by the STR market and would like to connect to see if I could add value to someone in their business or help (Co-Host) managing their STR.

I believe you would look at market analysis of what tenants would be in each of those scenarios and compare the proforma on each. 

Toledo is ranked #1 for 2024.https://www.cleveland.com/news/2023/12/ohio-town-ranked-no-1-us-housing-market-of-2024-realtorcom-says.html

And I should mention that I operate primarily off-market, so I've been thinking about diversifying into another market. 

I got this property at the right time, it was on the market for $699,000.00, seller needed to sell, I offered $550,000.00 after they cut to $650,000.00 and we agreed on $600,000.00.

I am currently in the market for land where I can build a new construction (ground-up construction).I recently read about the HomeStyle loan on BiggerPockets and wondering if anyone in Chicago has had experience they can share?

@Kevin Michel I'd work backwards from your skillset, amount of capital you have (or can raise), and the market you're interested in. 

It appears that a significant portion of the business's value lies in its name, website, marketing, furnishings and other intangible assets.