I am going to factor that into the asking price, the homes are older and with the 2 being uninhabitable to factor that into the offer. 

The location would probably be on the bottom of the list of importance, you need to look at other factors such as experience, quality for client service, etc.Second, as a self-employed real estate professional you should consider self-directed Solo 401k, which is much more superior to an IRA for several major reasons, you can read more on this blog post: http://www.biggerpockets.com/blogs/2810/blog_posts...

That is going to be a huge factor when speaking with your attorney and accountant.  

Those might be old relationships or new ones, but our first cull factor is that the prospective borrower must be someone we like and trust.

What factors are critical to making the deal work for me along with hopefully a higher acceptance rate from seller?

The condition/composition of your road will also be a factor in this.  

Not saying he is wrong because he is involved with more "wow" factor rehabs because of the area he is investing.

What factors influence their decision to sway this in my favor?

I used those things as motivating factors to be the reason I made it. 

Accurate prices are hard to come by because it depends on time of year and local factors.