Lucrative is a relative term. You're generally limited to two examinations a day. If the weather is bad you don't fly. You pay your own insurance, travel for required training, etc. Also consider most examiners give a discount for a retest.
Also, you don't log any of the time giving checkrides (unless you're serving as a required crew member). You spend 10-20% of your time delivering disappointing news, and get to enjoy regular observations from FAA inspectors.
It's not a bad gig, but you're not going to get rich at it either. A seriously hustling examiner probably makes about $150k/year, which isn't bad for a flying job, but it doesn't leave a lot of free time to fly yourself.
As far as being political, I'd say a good DPE candidate will be active, participate in FAASTeam events, not crash planes, etc. it helps to know other well regarded DPEs. There are a fair number of DPEs who have regular flying jobs too. I also agree with the other poster who mentioned that having less common ratings such as rotorcraft, gliders, LTA, gyro, etc.