I have had a lot of wrestling matches with this one. First, I'm assuming you are using a PC. The only issues that I have had with Macs is the wrong board or programmer selected.
If you are using a PC, there maybe be one driver issue your missing and/or PCs take to damn long to compile the code and the Trinket times out.
Driver issue - did you install the Trinket USB drivers? If not download the drivers
here. Click on the USBTinyISB.
Timing issue - Couple of tested and untested solutions here:
1. Press the UPLOAD button in Arduino IDE, wait about 5 seconds (+/-) then press the Trinket reset button.
2. Talk to Adafruit about a patch to the bootloader that will increase the 10 second windows to upload the code to 20 seconds.
5. I read this morning that Arduino just releases version 1.6. This may help as it said that it will autodetect the board and port.
6. Get a Mac to program the Trinket.
Good luck. Let me know what helps and what doesn't. It's been very frustrating. BTW, some of the Trinkets I've purchased were supposed to be 16Kz but are 8 and visa vera, so try different settings.
Feel free to contact me off list.
David Held
Poughkeepsie Day School