I know, which is why I'm taking it upon myself to combat this "fear" I guess you could call it.I guess what I could do is try to always keep a piece of paper near me, on that paper have a ballpark idea of what I am looking to spend, and what area I would be most likely be looking into, as well as how would I go about financing (now on that part, I most likely would want to work with a broker, since there's a bit more flexibility) since I would be going from "rags to niches to (hopefully) riches."

When you correct something that the lease does require of you, prepare a fill-in-the-blank form that you have them sign each time that shows the date that they brought the matter to your attention, briefly describes the matter, shows the date it was fixed, and states that their signature (make sure it states one party signing is sufficient) shows their full satisfaction with the action you took. 

No reason a tenant should be unwilling to confirm some thing that is already determined (rent amount, sec. dep amount, etc.).The estoppel really protects everyone - the seller, buyer, tenant and any agents or 3rd parties involved in thew transaction.Definitely not just for lenders.

I like that you receive cash flow every month, cash at closing, and have the ability to assign the deal to another party. 

Am I being too conservative?  

Strong conservative bias clearly seen. 

If it's a flip, just do a joint venture agreement and define each parties roles in detail.  

My numbers are run with an FHA loan that considers factors Is the 50% rule too conservative, or are there simply not good buys right now in Chicago.

The place we typically use has $250 closing costs but is extremely conservative.

I'm in the process of building a joint venture credibility package and going after JV opportunities however need some advice on where to start.We've had a busy 3 months securing 5 properties which has tapped my partner and I on approvals.I'm a big proponent on the old adage that each party must bring something to the table.