I put this together in the last few days after thinking about this topic some more. I wanted some way to race the Jenny, and I think this is definitely, well, one way to do that!: Aravaipa Canyon Run » Microsoft Flight Simulator
On the topic of timing, and verification of times, well, there’s actually a fantastic option built into MSFS that while buggy, hidden, and poorly documented, does everything you need to verify either solo or group races - the built-in replay tool.
If you go into settings → general → experimental you’ll find the options there (and then do this every time you launch the sim because it STILL resets, for some reason…). You can then record your runs or laps, watch other peoples runs, and time, verify, and watch even group events, since the tool records other traffic as well, or at least should - I haven’t tested that aspect much yet. The tool even records the camera track that’s used in the original flight, so you can prove that you never went external, for example, or if you’re in VR, prove you didn’t move outside the cockpit for a better view, it shows exactly what you saw the first time around.
Some notes for first time users - saving and loading takes an eternity, and it will look like the game is frozen - it usually isn’t. You can generally record from startup, but be sure to stop and save the recording before you shut down. Even if you have the option to display it turned off in the settings, the moment the logbook would have popped up, you lose the recording. Don’t crash (plane or sim) either, that wipes it too. Once you’ve saved a recording and loaded it back up, you’ll want to scrub through using the default camera track, and then use the record button under the camera track section, lower down, to free you up to move the camera around. And finally, loading and watching a replay seems to break the sim fundamentally for that session, so be sure to restart if you plan to go back to any actual flying, or you’ll find switches not working, throttles frozen, etc.
As an example, here’s a replay of me running Pima Canyon in the extra 330: PCR Extra 330.ReplayDesc - Google Drive