Man as much tourists dollars as that county takes in, more fees are absolutely ridiculous!  

My wife and I a debt free and own 15 rental properties worth around 1.5 million (net after sale taxes). 

One of the car washes is in IL and the other is in Iowa so I'm not sure if I can represent myself in just the IL and does that mean that the listing agent would have to split his commission with me if I purchase?

Also, I have 2 years of flipping experience in Iowa.

Galena and Door County are  possibilities, as is Rochester Mn which is fairly close to our farm in Iowa.

Like other posters have mentioned - it will likely vary by lender - but generally most states will be OK with either Individual or LLC but there are a handful of states that due to various regulatory interpretations will require a LLC (or require a LLC to have prepayment penalties on the loan structure) Borrower = Individual or Entity AL, AK, AR, AZ, CA, CO, CT, DE, DC, HI, ID, IL, IN, KS, KY, LA, ME, MD, MA, MI, MN, MS, MO, NE, NH, NJ, NM, NY, NC, OH, OK, OR, PA, SC, SD, TN, TX, UT, VT, WA, WV, WI, WY Borrower = Entity only GA, FL, IA, MT, RI, VA (1-4 Units) Prepayment Allowed Vested Entities Only IL, NJ

I assume that most people don't want to make the sacrifices to achieve financial freedom and are perfectly content working for the man as it provides them an easy and comfortable life. 

My family and I currently live in a small podunk town in Iowa, which I truly can't wait to move from, and we rarely come across money like this (we're basically as middle as middle-class can get). 

I believe the Iowa market would have similar code requirements.

That includes that I as listing agent/broker may DECLINE dual agency or facilitator agency service unto a buyer.