The Big Obstacles - Cost, Time, and Distance

The "Big Obstacles" to a midcareer graduate school credential project seem to fall into these three buckets:
1. Time
2. Distance (related to time, but not quite the same thing)
3. Cost

Any others?

If your employer offers a fully paid onsite degree program for employees which doesn't require a boss signoff on every course, you should jump on that unless there's a really compelling reason not to. It's the best setup you'll ever get with respect to time, distance, and cost with that employer. Plus usually some bigwig at the employer has invested some credibility in advocating that plan and they'll appreciate you making them look good.

(Note: one doesn't see these so much any more, because they have a notoriously high dropout rate. Usually they start with a lot of people and end up with no completions or just a couple. )