There are 3 that I have my eye on that are fairly close in specs:

#1 - 29k miles / $20k / not Volvo Certified
#2 - 28k miles / $23k / Volvo Certified
#3 - 24k miles / $25k / Volvo Certified

I have a 2012 C30 R-Design that I will be trading in with 13k miles

#1 is at Carmax. I've sold a car to them before, but have never bought one. I think they mentioned I could save about $1500 on taxes if I sold/bought through them?

#2/#3 is from a Volvo dealership. I definitely like that the cars are Volvo certified. Not sure if they will offer me more for my trade-in than Carmax, but I know if would be beneficial for them since they could resell it as a Certified vehicle.

Assuming condition of the cars are all the same, and I my initial budget was more like 22k for this car, I certainly like the price of #1 and only has 1000 more miles than the #2. Is the Volvo Certified worth about $3000 more and 1000 less miles?

 

You could do better on the price. I googled 2011 s40 last night and saw many of them for between 16 and 19 grand. And many of them seemed to be at Volvo dealerships. Also check the cars history. I'd love to be able to do what your doing, but I don't think I'd get get much for a '01 S40 with 170,000 miles.