It really does depend on how much work you want to do, and how much cooking you do during the winter.
I am a lazy smoker and like the set and forget it of the ceramic cookers. A WSM is a great choice and fits your price point.
Before you plunk down your cold hard cash, do a lot of research and take into account all your requirements, even if it means you need to save your pennies a little longer.
Official Pennsylvania MOINK Ball maker
1 Large BGE - 7/5/08
1 Large BGE and table - 8/29/12
1 18.5 new to me WSM
Super Fast BLUE and RED Thermapen
1 - The Great Outdoors Smoker Sea Bug cooker
1 - Fantastic hubby - the original Big Al
Enjoy the little things, for one day you may look back and realize they were the big things. - Robert Brault