Try as hard as you might, there's no guarantee you can win. What happens to "win, and keep winning... and then never lose again", if you never "win" the first time? The US political system is rigged (arguably by design) to favour conservatives. To successfully undo that rigging requires not just winning narrowly, it requires winning decisively. But how do you win decisively when the system is rigged against you? It might be about to get even more rigged–if the upcoming SCOTUS decision in Moore v Harper embraces the "independent state legislature theory", all efforts to prevent gerrymandering by state legislatures would be dead in the water. So, what if you don't win, what if you lose–what then do you do?

And even if your wildest dreams come true–if you win too big, the other side may turn around and say "democracy isn't working for us any more". If it gets to the point that a significant minority of the population (say 20-40%) no longer believes that democracy is in their best interests, democracy's days are numbered. Especially if that significant minority has a great deal of wealth, influence and power. It could end in the peaceful negotiation of a "national divorce"–and there are many worst ways it could end than that.