I'm a fan of the travelmate when in the kinds of situations where one has to be very neat about it i.e. where you can't do the wide-shorts-pantleg freehand/standing maneuver... It takes practice either way. There's a definite learning curve with either method... and even after you get 'good' you can still slip/drip sometimes. Not good. Everyone's anatomy's different but I find the best leak-free use is between the labia minora, right over my urethra. (I'd say TMI but how else does one word these things?)

When at outdoor fairs and the like, I use the travelmate and the portapotty urinal. I carry a bottle of alcohol with me (or vodka? depending on the venue...) and of course a camelbak of water (those outdoor venues are hot...=P) so after use it gets a quick flush with alcohol then a rinse with water, a shakeoff and goes into a baggie.

Bear in mind- urine is essentially sterile *to you*- HOWEVER due to the mineral/salt/sugar/protein contents, it breeds bacteria quickly... so you don't have to act like it's poison or anything, but be sure to give it a decent rinse-down.