When will the size of the electoral college change again?

When Puerto Rico or DC become states. Each would add two Senators and draw from the pool of Representatives (replacing DC’s third elector).

> When will the size of the electoral college change again?

When:

(1) One or more new states are added, or (2) The law fixing the size of the House is amended/replaced.

I wouldn’t be surprised if those happen together, so that adding the new state adds on rather than redistributes seats in the House initially.

Note that D.C. being added (with no change to the fixed size of the House) as a state would actually shrink the electoral college by one, since it would add two Senators and zero reps, but D.C. already has three electors; any other state being added (with no change to the fixed size of the House) would add two electors for the two additional Senators added.

Or in theory 3) when the Constitution is amended in a way that changes the makeup of the electoral college, but in practice that's much less likely to happen than the other two (which are themselves unlikely to happen soon).

Ha!

Now you've got me genuinely curious as to whether launching e.g. FiveForty would be considered trademark infringement by the courts.

My hunch is it would still be infringement, since it's similar enough. In the same way Pepsi wouldn't be allowed to launch a cola called Coky.