Yes, but the problems become bigger with the complexity of the system. For you that is not a problem as you keep it simple. I asked professional programmers to automate my system, but that seems not to be so easy. Automation cannot solve everything, if it would, nobody would work anymore, robots would do everything.
An equally interesting question is - would you retire completely once you hit your target number? I hit mine a few years ago. It's a strange feeling but I can't seem to want to step away - I get too restless.
I remember an interview with a guy studying UHNWIs, and he reckoned those rich folks tended to always feel they didn't have enough money, with the double of their networth often cited as the amount needed so they would feel safe financially. Otherwise i share your sentiment, I already passed the target i thought would be great to live off only a few years back, but early retirement meaning getting injured playing tennis than reinjured playing golf, with some pool injury in the middle rythmed by quite a bit of homework with the kids while enduring all sorts of joint pains gets boring. Looking to make more money seems like a decent alternative, plus it's non exclusive, one can still sprain a muscle or break a bone merrily while looking for business opportunities.
Once you've reached your number you don't have to sit down and never get up anymore. You can still be active. However, the motivation/purpose/goal for the activity has changed. It is no longer intended to generate income, but to have a good time and feel satisfied. For example: instead of going to do a job daily, you now can spend your time on volunteer work for a cause you support.
I don't get the whole volunteering fad. If I'd go and serve at a soup kitchen or go clean cages at dog shelter, I would be doing work that pays the minimum wage. So, from the productivity perspective, I would be throwing out X dollars for every hour I volunteer. Instead, what I actually do is donate a big fraction of my income so those organizations can hire people or use that money in other ways. I have been steadily increasing the portion of my income that goes to the "causes", my aim is to reach 45-50% of my income (maximum deductible) in the near future. It's a surprising amount of work, hassle and stress. First, it takes an effort to figure out where the money should go, most non-profits are either ineffective or an outright scam, and it's unclear how to measure what "a good charity organization" is quantitatively. Second, there is smoothing the allocations - right now I use donor-advised funds but might switch now that I have access to self-invested charitable foundation. Third (an odd one), is saying "no" to the ones I don't like, it's amazing how many phone calls or emails I get. PS. Edited out stuff that apparently caused butthurt in some members of the community