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I know people who regret it, and I turned down an in house offer a while ago after talking to colleagues who made the move. They didn't all regret it, but they all agreed that I would.
It depends what part of the job you enjoy. I enjoy building strategies with clients and then executing by writing the patents. Some people hate writing the patents. If you move in house, you get to do more strategy (and sit through more meetings) and write less. If you currently work for multiple clients, you may miss the variety.
As far as transitioning back, we have interviewed people in house and turned them down because we didn't know how they would do when they started writing again after not writing an original application in 5+ years. We are just one small firm though, and firms are different.
I started in-house, and just barely transitioned out to a firm. I was doing a lot of drafting and prosecution - anything outside of that was "extra" stuff to get noticed for promotions. In-house is pretty boring and rote. I didn't realize how bored/depressed I was.
Keeping time sucks, but I'd rather do that and have interesting work than be a cog in a machine. Other in-house positions at other companies might be more interesting, but mine was a real slog, and I didn't grow/learn much after the first year.
Yes and yes! Actually, years later I was able to see it as an important learning opportunity. There are definitely firms that would love to have you because of your in-house experience. Also, I have seen in-housers ‘use’ boutique IP firms as a safe landing space in between jobs, and the firms don’t mind because they see the benefits of building relationships.