you can't buy land with financing if you don't have the cash to purchase the land you don't have the liquidity to do this type of project. rule number one. we sell 10-20 land plots a year and all of the investors have 2-3x land cost in equity / cash that they can purchase directly. that's before all entitlements and everything else 

A prudent investor doesn't seek quick riches through shortcuts.

I would have been told by someone about index services (with correct hours) before spending $40 in postage to overnight something to Springfield.Hope my experience helps a fellow investor.

I've got about 7k in an emergency savings account.I am in the process of getting several mortgage pre-approvals to compare fees and get an idea of how much home I can realistically afford.I have yet to find a buyer's agent/investor to help me identify potential homes but will start on that shortly.Ideally, I would like to buy a single family home.

Though many investors bend the rules and possibly don't get caught, you have the financial situation to do it correctly.

Your question is one that most Chicago investors, including myself, have gone back and forth on many times. 

You can test this, by asking some to SHOW you how they calculate ROI, Cap Rates, Cash-on-Cash, etc., for their clients.Many will say, "that's the investor's problem".They are correct because an investor should NOT rely anyone else to run their numbers.So, then what exactly makes them investor-friendly?

I suppose they would be able to help me figure it out but I’m still trying to determine what is the best way to fund something like this and would it be better to sell off the entire purchase once split into separate parcels or is there a way to structure a deal as to where I could sell off some of the land to repay the loan/investors and also retain a portion of it to develop with my own short term rentals.

I have no interest, and neither will a majority of investors. 

Mark, since you're an inexperienced investor, I would be very cautious about borrowing against the roof over your head.