I frequently get bills from him ranging from 50.00 for a minor fix to $1500 for more major items.

I'd like to create systems in these markets to be as hands-off as possible, but at least in the beginning stages, I will be visiting these areas frequently and would like to enjoy it!

I am looking for an agent that works with investors in the Chicago area frequently who could direct me to a solid lender.

@Kyle NelsonOne thing you might want to take into consideration, whether or not each jurisdiction/city will allow air bnb, or the frequent rentals to multiple different people.

My goal is to find sales within 1/4 mile and 6 months, but I frequently don't have enough data without pushing out both radius and time. 

Do not apply for more credit too frequently.4.

It sounds like you came across either a lazy agent, someone who doesn’t frequently work with investors (most agents don’t), someone who has a poor understanding of providing exceptional service or someone who doesn’t feel you’re in a serious enough mindset to purchase (doubt it’s the last one, just letting you see the whole field of view from an agents perspective).

If you find something that you believe can't be fixed with a limited outlay of funds, you will lose your deposit, which is frequently 5-10K. 

It would be easier to have a larger park with more income..If your thinking about it make sure you have the proper reserves or insurance.. and make sure you dont cheap on your due diligence on evaluating the well and septics and know the replacement costs including replacing the pumps.. and how frequent the well needs to be monitored to abide by EPA standards.. 

Guess I'm either lucky or valid property liens are less frequent than I ever realized.