2011 KW T660 or 2011 Freightliner Cascadia for OTR?

It's the flatter one only 12'6 high and 53 flat usually 40000 plus on it and it's a 13

 

KW with DPF.

 

In five years, the truck is expended, as far as most companies think. Don't think about "resale value." You're either going to spend the money to keep it running well, or you're going to get peanuts for it, no matter whose name is on the front.

You also have no idea what the resale market will be like 6 months from now, much less in 5 years. Sometimes KW is up, sometimes FTL is up, so you can't expect even to be able to sell it at ANY price, except as parts. Let's say that, after 500K miles, one is worth $5,000 more than the other. That works out to a penny per mile, which is less than you'll save by keeping your tires properly inflated. What you want is the truck that you will prefer DRIVING those 500K miles. I wouldn't take a KW if they promised to give me an extra $20,000 for it in 5 years, because that 4 cents per mile isn't worth the quality-control problems I've seen in KWs, or the narrower cab and less interior room.

Get the truck that fits you NOW. Sit in them both, without moving but hands on the wheel, for an hour. Is either more comfortable to you? Are the controls and gauges where you want them? Can you reach storage from the seat, for your munchies and other stuff that you might want to not stop to get hold of? Then lay in the bunk for 10 minutes and see how you perceive the interior space. That space will only get smaller over the next 5 years. How is the storage? Where are you going to put your microwave, your DVD player, your jacket, your groceries, your tools?

Trust me, that extra penny per mile that you may or may not see 5 years from now ceases to be important if those 5 years are spent wishing you had a different truck.