Not wanting to look into smaller towns or communities up north I assume it'll be a tough battle to find something worth while that doesn't need too much work.

This helps me track net worth.

Then buyers will be looking at your postings first.My personal record for a killer deal for me AND the investor22 hours from me signing the option ( buy) paperwork to signing the assignment$50 ( fifty)… five…oh… FITTY dollars out of pocketMy “ option to buy price”..$15,000My “ Assignment fee” …$. $17,000Assignment deal completed 22 hours after I signed the initial docs.Sound like a rip off?

You can most certainly get a loan on an investment property....consider connecting with @Landon Hoon or @Michael Barbari both local Chicago lenders.If you are looking for maybe something a bit more aggressive on the down payment with hard money let me know and I can provide some other contacts.Partnering will be the best way with no money...it's not easy and you'll have to be willing to do all the work...but worth it in my opinion.

I invest in Jacksonville FL where the homes are worth in the low 200s.I find that CPAs will tell you to have one LLC for each property... maybe because they can charge you more per tax return :)

Before U get to far into this deal you could pull public records look at the existing mortgage and or Deed of Trust and see who the beneficiary is this will tell you a lot very quickly if you simply cant ask the seller what his terms of his existing mortgage are.

He is definitely "the real deal" in terms of he is a very successful entrepreneur with a big net worth and several streams of income (one of them being these future flipper course sales).Here's my 2 cents. 

One lawsuit is worth having the insurance.

Wondering if its worth it, as I know the development process and have good civil, architect and GC contacts.   

DSCR loans won't use your income to underwrite the loan.DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.