Choice is your's Patty, on when to raise the dose, with your days off that you have coming up. If it were me, I'd do the first available day off to increase.
1. Have you considered using a CGM (continuous glucose monitor)? I've seen more comments about people using that for their cats. The libre has been mentioned. The only things I know about it are it's expensive, cat's can dislodge it, lasts for about 2 weeks, fur grows back and then the monitor can't attach as well. Might be something to consider, especially with your time away coming up and Teal'c being boarded.
2. Do you remember when you did the food change from Fancy Feast and Friskies to the Dr. Elsey's?? Roughly, the timeframe. Trying to see if that food change had anything to do with the need for increasing doses with Teal'c.
3. Convince Bobby to test every night before he goes to bed, at Teal'cs PM +2 time. Gets you a bit more data. What if you get sick? Will Bobby test then or would you have to do the testing still?