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.

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.

If you are conservative with your numbers and build in a buffer, you'll be fine.