> Yet this job is oddly comfortable (in terms of benefits)

I once walked away from a gig that was literally 2 blocks down from my door and traded it in for a gig with a 2 hour commute. Just to guard my sanity.

I think it comes to to cost/benefit and opportunity cost calculations. And those are different for everyone.

I have been looking around for a new opportunity, but I haven't come across any that made me comfortable enough to resign from my current job. My fear is that it will just be the same thing, and in that case, I might as well stay where I'm at.

It definitely won't be the same... "all happy families are the same, unhappy families are each unhappy in their own way. "

Forget where that's from, but seems true of companies too. Each company I've joined had skeletons you'd never see during an interview. After the honeymoon period wears off, the truth starts to show.

Not to say that you shouldn't find a new job. Definitely don't expect it just get better though.

In fact trading the known badness of your current company for something else gives you opportunity to find different ways a company can be dysfunctional. Enough of those experiences and you'll get good at pointing out dragons before they get nasty. Truly valuable for a senior developer.

Your anecdotes remind me of what I've heard about in-house counsel: lawyers can tell you that you should/shouldn't do something, but in the end, lawyers don't run the business, and sometimes they get ignored.

I think that in software there's something similar. Maybe you'd have more fun in a software company, where what you do is central to the business. Anyway, don't give up hope! There are jobs out there where you'd be having a lot more fun every day.

> I've lost all respect for people who operate as the middleman between the development team and the business side, mostly because when it comes down to choosing a side, they'll side with the business, and play their politics game.

Don't let this stereotype poison your career. Not everyone is like that, but if you assume they are, they likely will be. Relationships are so key.

Sadly I’ve met so many of these people, that my default assumption is that everyone is like this.

I’m sure there’s good ones, and I really hope I get a chance to work with them.

Like the good cops versus the bad cops, they don't stand out. And they won't be advertising how hard they are working for people like you. Search them out, and give people the benefit of the doubt.