Does the bar out the front have to be put up every time you set up or is it left on the boat even when trailering?
Yes, the bar (spi pole) has to be set up every time you rig as it is supported by the main bridle. It is usually attached to the front crossbar with a pin.
When you come about from a run how easiy and quickly can one actually get it tucked back into the pouch?
If spinnaker rig is set up properly and properly tuned, the retrieval of the spi into the pouch (snuffer) can be done quickly with some practice. In racing, I think there's a rule that if it takes longer than 6 seconds, you're doing something wrong. However, in recreational sailing, you just want to make sure you don't get it caught up in any of the rigging. Timing is important.
Lastly is it a worthy investment?
The answer to that question is relative. How much fun are you going to have and how much is that fun worth. First, it's not class legal in the US (don't know about Canada) so it would have to be strictly for recreational use.
The fun factor??? On that issue, for me, I'm kinda like Karl !!! Now that I've had one, I can't see having a boat without one. It's like having a completely different boat. Downwind, it's like sailing a runaway freight train and I haven't even sailed my spi in high winds yet !!! (contrary to popular opinion, the spi decreases the H16's propensity to pitch pole but that doesn't mean that it won't)
It can also add to the fun factor when there's very little wind, a good time to practice, by the way. All being said, I would make sure that my sailing skills were adequate in sailing without one before attempting to sail with one. There's a definite learning curve involved that throws some of what you've already learned out the window. Well, at least it may modify it somewhat !!! http://www.youtube.com/watch?NR=1&v=66DZB5bhg2s