Regarding 2020, the quality of Trumps lawyers, etc.
The problem with 99% of the cases was standing. William Barr explicitly told Trump this would be the case, that lawsuits and objections needed to be filed prior to the election, and he didn't listen.
Every single state that changed their voting process to allow vote by mail en mass did so without amending their laws/consitiutions with a vote in the state house, nearly all of them merely pointed to other states doing the same, something most state constitutions explicitly rule out as a justification as states are supposed to excercise a great deal of independence on how they individually run their election.
This all occurred, of course, when the revered Dr. Faucci said that in person voting would be safe. The one thing out of this guys fucking mouth that wasnt adhered slavishly or listened too and instead we got the mess that we got.
Though tbh, Trump not backing down and winning in 2024 was almost worth all the bullshit. Almost.