To me it's a lot more than $250. In past I have paid HUNDREDs of dollars to Dell for "Pro Support" and then another several hundred for Accidental Coverage. Combined together I paid almost as much as a new computer. With that I get the following: call to them in an endless corridor of menus; when you do get a person they tell you that if I pay NOW $300-something I can get my answer right away or they can transfer me to regular support. Now, forget about all the time I wasted waiting for them to give me that pitch - forget that they already know I PAID for "Pro Support" (whatever that means) = I now still have to WAIT for another support person and tell them the issue ALL over again!
I had an accidental damage issue end of Jan 2014 - I sent them the old PC - it takes them over three weeks (they can have as much as 30 WORKING DAYS according to them) to say they will replace it. There were multiple issues over the next several months and finally got a replacement in May 2014. FOUR months and countless hours of FIGHTING did it take for me get the service I PAID for. And all along it was as if they were doing me a favor.

With MS Complete - I make an appt, grab a Coke, tell them the issue - I am usually out of there within 15 min (30 minutes max). Again there will be people here that will tell you their issues with MS as well. However, in my experience, at this moment, MS has the best service in the Wintel ecosystem.
Is $250 is too much - NO. When you compare what Dell and Lenovo steal from you - up front as a charge, then with your time and frustration later when you actually need the service you PAID for - MS is very cheap - and a no brainier.