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Now that the current Supreme Court has ruled that Sec. 3 of the Fourteenth Amendment doesn't count because Congress has not passed enabling legislation, Trump might be thinking that the Twenty-Second Amendment might also be invalid for the same reason, so if he wins a second term, there is nothing stopping him from running and winning a third term in 2028. Then, when the electoral votes are counted on Jan. 6, 2029, the president of the Senate could create a constitutional crisis and a friendly Supreme Court could say that the Twenty-Second Amendment is not self-executing.
As candidates for vice president on the Republican ticket jockey for position, a new litmus test has arisen: Candidates are now having to answer the question of whether they would have certified the electoral votes on Jan. 6, 2021, had they been President of the Senate then. This is a proxy question for: "If Donald Trump does not like the results of the 2028 election, will you certify the electoral votes as they are counted on Jan. 6, 2029?" Hint: The correct answer is: "No."
The 2029 situation won't be exactly the same as the 2021 situation because in 2022, Congress passed the Electoral Count Reform Act (ECRA). The new law specifies in more detail what happens after the states send their electoral votes to Congress. Among other things, even to raise an objection to any state's electoral votes, one-fifth of each chamber must lodge an objection, up from one member in each chamber in the original 1887 law. It also specifies that the role of the president of the Senate is "ministerial," although it doesn't define what powers, if any, go with that. It also says Congress must defer to the states. In addition, the law says that the slate of electors submitted by each state must be signed by the executive authority of that state. The legislature of the state can determine who has that authority, typically the governor or the secretary of state, and it can't change the rules after the election. Finally, the ECRA requires (unspecified) security features to be built into the actual document (the certificate of ascertainment) that is sent to Congress to prevent forgeries. This link gives more detail on the whole process, especially on the state's end of it.
As a consequence of the ECRA, on Jan. 6, 2025, President of the Senate Kamala Harris and whoever may be president of the Senate on Jan. 6, 2029, will have a lot less freedom in rejecting electoral votes, unless they don't mind breaking the law and seeing what happens next. Trump's litmus test is effectively asking the candidates if they would be willing to break the law if he asked them to, which would create a constitutional crisis in the process. Maybe he is thinking that with a friendly Supreme Court to make the final decision, he would be willing to create a constitutional crisis in 2029 and wants a veep who would be willing to go down that road. (V)