There are of course many work arounds, one of which, I reason, is to get my license so that I can do step 2 in my own time, putting in whatever time and effort I feel is required without asking for favors.

It might appear like they are doing you a favor by offering the loan in such circumstances, but if you are stuck in a position unable to meet the terms of the loan your credit and financial solvency can be negatively affected.

I have already began collecting contacts and was wondering if anyone had any advice on how to keep track of them and if anyone has a favorable app they use, ect. 

Also be prepared for the fact that the court is as likely to rule in his favor as it is in yours....which means you could conceivably end up owing the seller and the courts thousands of more dollars.

The one thing I do have in my favor is the fact that I am relatively familiar with Fannie Mae and HUD purchase procedures and am registered buying agent with them.

And, while rental rates in our area are strong and have risen nicely these last several years, I would recommend you consider that our rental rates and/or vacancies might not always stay so favorable.

You don't learn you market online.Regarding startup capital; either find a partner or do it the old fashioned way - save it up.

I may end up with the property due to foreclosure so I wanted to seek advise from any investors out there in Gary about what is the most favorable exit strategy for that market. 

Meaning, I don't have to necessarily provide them evidence of current title insurance....just sufficient evidence that the title is clear.9c(iii) seems more favorable to the Seller than 9c(i), since the language in 9c(i) is the following:Seller shall designate Closing Agent and pay for Owner’s Policy and Charges (but not including charges for closing services related to Buyer’s lender’s policy and endorsements and loan closing, which amounts shall be paid by Buyer to Closing Agent or such other provider(s) as Buyer may select);It seems to me, that 9c(i) is implying the Seller would pay for the Owner's policy, which could amount to over $200.  9c(iii) limits the Seller's responsibility to $200 to simply cover title search expenses.Any thoughts?

That's about the point where your second property cash flows down to zero.If you want more borrowing capacity then get another HELOC on more favorable terms, at least on the first property.