Subject-To Deal in Colorado Springs

[Storm Daniels]

I have someone who has contacted me and we came to an agreement that involves him selling me his house in Colorado Springs subject to his existing financing.  He has some concerns about certain things and so do I that may not be standard questions given that I am completely new to this, so I thought I'd come here to share the situation and see if anyone has any input for me.

So the numbers work out to my standards and we are agreed as long as I come up with $25k. The seller has concerns about his VA loan benefits being tied up in his current mortgage because he believes he will need to use those benefits in about 2 years from now. I don't know how refinancing would work in this case, because the title would be in my name, but I would not have an existing mortgage on that property. At that point I would have a history of rental income coming in from that house, but the balance of the loan would not be on my credit. What should refinancing look like in a situation like this? Would 20% of the loan balance need to be brought to the table, since this is technically a new mortgage in the eyes of the bank? My alternative to this would be to sell the house if refinancing at that time would not be an option. In this case, I would not lose any money, so it is a reasonable exit strategy if it comes to that.

My other concern is finding someone to facilitate the whole process.  I can find the paperwork to use and fill it out and everything, but I wanted to try and get a handle on what other things are necessary to make the deal go smoothly and to minimize the risk we both take on.  I'm working on contacting my Realtor and perusing as much material as I can on this, but I'm determined to make this work if it can.  Any information is much appreciated!  This is an interesting opportunity for me to learn more about how a subject to works in detail while allowing me to get my hands on another rental property in the market that I like!