I would agree that for Scott, it's a big move and a bold statement to subject himself to an interview on the topic. 

Luke Texidor That is a bold and unnecessary move, when you did an interview/walk the contractor, you should have a paper that will spell out what you want done, per room or per line item or both, that way, you will simply have him sign it and incorporate it to the contract.

I put my responses to your questions below in bold:-Do you recommend any loan officers or real estate agents in the Chicago area who have experience creating successful outcomes for people with goals similar to mine? 

That's a bold assumption.

Just like driving a car, it is not illegal to drive but you can perform it illegally.No meat on any bones - That is a broad and bold statement, while I agree with you that the market conditions in AZ are fully on the side of sellers not buyers (this is the case in most areas across the country and even more prevalent here in So Cal), this is not to say that there is no such thing as a deal, you just have to get creative and go after more quantity to land that one deal.Your list statement - absolutely true!

Looks like I'm late to the party...I'm assuming you've already found something at this point, but if you haven't, I have a suggestion for the bold that is the opposite of most of the advice I've seen in this thread; at 300k your best bet is a fourplex on the East side, 78724 area.

I am in the largest producing real estate office in Indianapolis and I regularly train new agents including all the ones that go to BOLD.

"Dumbest thing you can ever do" is a bold statement, but I respect your opinion. 

Hi everyone,I know this is likely the overly-obvious, "goes without saying" question to ask around here, but I wanted to be bold and ask it anyways. 

I've bolded the correct line above and agree with this.