Worry Free is kind of a hit and miss.
Pros-
-They use a great product/system (GAF). For what you'll pay extra for with another company is included in Worry Free's base estimate. This includes a Maxi vent, GAF Timberline shingles, GAF deck armour, drip edge, etc. Most other companies use IKO or BP, both of which are garbage. The only other I'd recommend is Certainteed, which Worry Free also installs and for less money.
-Denis, the owner, is a stand up guy. I had some issues and he was very polite, understanding and took care of the problems.
-The crews seem well trained, though the quality of work they do seems to vary greatly from crew to crew. When I talked to the guys they had about 7 crews so they're able to whip off the houses pretty good. The team that did my house had about 7-8 guys and finished my house in about a day. The crew that did my neighbours homes was only 3 guys and took about 1.5-2 days to do a house. They seemed more meticulous though. So YMMV on the crew you get. They also told me they shoot about 6-8 nails per shingle, where typically it's around 4 in the industry (I think). This just means your shingles are far less likely to blow off.
-The price was very reasonable. For the quality of products they use they couldn't really be beat.
-GAF certified contractor
-Group discount for multiple homes
Cons-
-Communication is abysmal. They told me they would come on a Monday so I took the day off to stay home. They never showed up and never told me they couldn't make it. They showed up on a Wednesday out of the blue. (The weather was beautiful for about a week straight, so weather is no excuse.)
-The crew that did my roof seemed young and inexperienced. I wasn't able to stay home and watch what they were doing, but I heard from my neighbour a few things I didn't like. They were pretty vulgar for one and seemed to pay less attention to details compared to the other crew I watched.
-Matt, the salesman, is very knowledgeable and nice at first, but once he closes the deal you'll never hear from him again. Ever.
-The cleanup wasn't the best. I found about 20+ nails on my property, about 7 of those were on the driveway.
-Matt never included an estimate for the drip edge on the pink slip, so it was never ordered or installed on my house when the roof was as a result. They had to come back later and add it, after I noticed and called them up.
-I walked the roof and found a box of staples on the maxi vent (wind could have easily blown it all over my property), nails all over the roof and some flashing wasn't put back properly. In the end they had to come back to fix some things, but they did.
Conclusion
Worry Free isn't so "worry free". They use great materials and can produce a great result at a reasonable cost. I'm very happy with the way my roof looks and I have no concerns about leaks for many, many years. While the effort and frustration it took to get to this point was more than I wanted, I'm happy it's done and am very pleased with the cost and look of the roof.
If I had to recommend one thing it would be to make sure they spell out _everything_ on the contract - product name, quantity, etc.
P.S.- I know about 6 others that went with Worry Free and didn't have any problems.