What a thoughtful, well thought out question, Josh!
In my article series, "Am I Ready For an Online Education?", I outline several things that people need to consider when thinking about starting an online degree or course such as: degree programs, organization, expectations, and soon another article on time management.
Besides those issues, I think it is very crucial to think about the end result of a degree before you start one. One of the things I did before going to grad school was to talk to potential employers about which universities they thought highly of. It's not always the Ivy League schools that have the impressive reputations. In my case, Framingham State College (my undergraduate school) had one of the best reputations in the state because it was the first state teaching school in the country. Even though it was a bargain compared to universities, it was thought of just as highly.
If you don't feel comfortable talking to the employer/boss of potential jobs then you can also seek out their employees. Many times employers hire a lot of people from similar schools because of the school's reputation or because of social networking. Either way, finding out that information could lead you in the right direction.
Unfortunately, online degrees are fairly new so many schools don't have the right reputation or recognition for employers. A safe bet would be to get an online degree from a school that also holds traditional courses on a campus. For example, Norwich University is a well known military school that has slowly become more of a civilian school over the years. They still have a tremendous reputation, but now offer online degrees such as a Masters in Criminal Justice.
Ultimately, a standard university may be your best choice if you are unsure of computers, worried about a college's ranking, or advancing your career. However, if you are at all interested in an online education then I think it is definitely worth your time to do a little research to see if it is right for you. After all, you'd put that same effort into a standard college, so why not put that same effort into looking into an online degree?