The first obstacle is finding out what the requirements are, what the demand is, and if any of my industry experience can be applied toward those qualifications. This topic came up in the team at work on Friday as well and one person mentioned that they had done some teaching at the community college without a degree just due to industry experience. If so then I'll have a much better shot of making it happen without going back to college for 4-8+ years.
I'm also starting to feel that going to a academic environment would be a nice break from the corporate environments of late. Something about having an actual campus, and not just a work cube, seems attractive. An environment that encourages discussion, and not just work work work, could also be refreshing. In that vein a 6-12 month period at a college (as a student) could be feasible. Too much more than that and it would feel like I was wasting time before doing something productive. I also doubt my cash reserves would last too much more than that anyway.