I work in a Windows environnent but often use Linux at home. I find that the level of difficulty is equivalent once you're familiar with either OS, their general design, and how their management tools are meant to work. It's mostly a familiarity problem. You don't use Windows regularly so you have no idea where to even start troubleshooting, or how to tell at a glance if the instructions you've found pass the sniff test.
Plus, it's always considerably easier to troubleshoot your own shit than to troubleshoot some random person's jacked up configuration where you don't know how they use their machine or how they managed to fuck it up.
The biggest difference I find is that Windows has such a massive user base that any "user based" help (like the microsoft support forums, yuck) is far more likely to be written by some shmuck that doesn't know what they're talking about than you see with Linux. Alternatively, it's just content farm site after content farm site regurgitating shit advice stolen from the users who don't really know what they're talking about. Finding useful information and guides can be more difficult.