Yes, it can be rewarding - did that myself for years. I recommend to specialize in a narrow and rare niche - so that you would be hired also by large corporation's IT departments, rather than doing 'all things IT' for small businesses who don't have their own IT team. In the latter business, I see more and more companies offering standard remote IT support at very competitive prices (and you compete with businesses worldwide), so I would not rely on that kind of business forever.
One legal aspect: In some countries you must not work as a contractor full-time for one company for years, but your contract would need to be turned into an employment or halted for some months (I guess you are from the US - this is a huge issue for freelancers in Germans now, but I am aware of one case in the US: Large software company allowed its contractors to have access to their networks only for 18 months, then you need to 'take a break' for 6 months). If you work as a specialist - only for a few days or weeks for a well-defined task - you don't have to consider that.