There are some areas that will never cash flow, rather where you will get a return on your money is through appreciation when you sell.

@Nick BednarczykI think people also need to understand that fed rates are not directly correlated to mortgage ratesMortgage rates are more in line with the 10 year treasury which could remain high if we continue to spend money like a drunken sailor

I’d recommend getting terms from private and hard money lenders.

I am a first time homebuyer looking to house hack in Chicago and I have an almost 800 credit score, but I don't really have much saved up beyond my emergency fund for a down payment.

Are you looking to lend your money directly?

As long as you can later prove that this money did come out of your pocket, no issue.As far as your logistics question, let's flip it and consider it from the buyer's side.

As a broke college student I can’t do much when it comes to money but I do have something even greater, time.

Lots of schedule Es I can not read or understand.I obviously know my rent "income" and my costs (especially since I make NO positive cash flow money on it and mostly loose money (last year I lost "only" -$1175) so i want to know what i made in appreciation versus how much I lost per year for the past 20 years. 

Execute a 12 month lease where you can collect a security deposit and collect rent to cover the mortgage and some money towards maintenance.

They normally run your personal credit report if I recall correctly unless you already accounts with them (I'm mostly sure)  That's why you can contact Chase for one of their ink business cards and say 'I think I'll make this much money' and i have a LLC or registered sole proprietor so please extend me some credit...however, I believe there are "true" corporate credit cards.