Have you ever seen it start charging later than the time you set it to start? That would definately be a bigger problem...
I now have a confirmed case of the car starting the charge later than scheduled as shown on the touchscreen. It was merely an inconvenience in this case, but could be a big problem in different circumstances.
I've been charging at 4:00 am recently. Sunday night, I was down to 122 ideal miles in standard and needed to leave the house at 6:20 to drive to Olympia, a 140-mile round trip. So I wanted a full standard mode charge done before 6:20. Estimating about 2.5 hours for the charge, I realized 4 am was cutting it close. So I went out to the garage where the car was already plugged in and used the touch screen to change the start time to 3 am, then verified that the touchscreen said "scheduled charge: 3 am".
When I went out to the car at 6:20, it was close to done but still charging. At 6:25, it was still drawing 17A, so I had to unplug it. The message on the screen said that it had charged for 2:25, indicating a 4:00 am start. Examination of the log file confirmed that it had started at 4:00 am even though the touchscreen clearly indicated it was scheduled to start at 3:00 am.
I was pretty annoyed that the error caused me to leave 5 minutes late and I still didn't have a full charge. I did have enough charge to make the round trip, although I was down to about 5% in standard mode when I got home.
I didn't change any settings and let it charge that night. According to the logs, it did correctly start at 3:00. So the changed setting did stick, just not for the first charge after the change.
Last night, I continued the experiment: with the car turned off, not plugged in, and the charge port door closed, I tapped the touchscreen and changed the start time to 2:00 am. Then I opened the charge port door and plugged in. According to the log, it started the charge correctly at 2:00 am.
So, don't count on changes to the charge timer sticking if the car is already plugged in. It seems like if you need to change the charging timer, the car should not be plugged in and the charge port door should be closed. Change the settings, then plug in.
My firmware is version 3.5.18, which I believe is the current version for 2008 Roadsters.