Baking in drinking glasses -- heat vs. logo paint, other issues

What you want to do has been done successfully. There is a video and instructions here:

Guinness Cake baked in Guinness glasses

I believe the greatest risk of thermal shock would come when you remove the cakes from the oven. Do not take the glasses out of the baking pan and place on a cool counter top (doing this can break some heat safe glass). Cool in the baking pan on a cooling rack or on a pot holder/towel.

As far as the painted logo on the glass, if it is commercailly produced, the logo would have been heat processed/baked on, so the heat in your oven should not be a problem.

Using drinking glasses, or even canning jars, risks the glass cracking, splintering, exploding, or shattering. Even a canning jar is not built to withstand oven temperatures higher than 120 C/250 F degrees. True, it's been done, baking cakes in a jar meant for preserving. Far safer would be to use tempered glass containers, which are designed to withstand oven temperatures as high as 300°C/572°F such as these ramekins on Amazon.

@ElendilTheTall has the best approach: bake the cake and pack it into your lovely, full set of Guinness glasses.

I'd worry that it's not going to rise and set properly. A pint glass isn't uniform. The bottom will set before the top does. There's a good chance you'll end up with something like a molten lava cake -- not necessarily a bad thing, but perhaps not what you're looking for. (And I would be very careful about serving it hot: people will expect to touch the glass, which will be very hot.)

You could try cooking it in a water bath, which will protect the logo as well. (If you could find one with an etched rather than painted logo, it would survive oven heat.) The top may feel a bit tacky at the end; conceivably a minute under the broiler (but set on the bottom rack, to protect the glass) would fix that.

Place the glasses on a cold, thick baking sheet would be more thermal stress.

Your best bet would be not to preheat and let it cool in the oven
Not best for the cake but best for the glass

Glass is pretty heat resilient

What type of glass? If it is Borosilicate glass (used in lab glassware and corning made PYREX kitchenware before the PYREX brand was sold) You should not have any problems as long as you handle your glassware carefully (Borosilicate glass is slightly more brittle than the more common soda lime glass but has better thermal properties making it a good choice for use in ovens and some stoves). Soda lime glass may also be acceptable if it is tempered but it requires a different type of care as it is less impact brittle but more vulnerable to thermal shocks.