I arrived in the Bronx with a camera, Flip video camera, Marantz audio recorder, laptop, mobile hotspot, and pen and paper, to live cover a “family values” march that was being held on the same day as the AIDS walk (in Central Park). I did not have an iPhone or live-streaming device.
I think our aim was good to have some interviews up beforehand to frame the debate and thought our choice of software (coveritlive) was a good one. 
One lesson learned, is to identify several elements that are critical to the coverage and get them before the event begins (either far in advance or before, in this case, the actual “marching” begins), and upload them to the producer or live module. This way, the producer already has in hand several elements that can be rolled out as if live, and the reporter is then freed up to collect more elements that can be uploaded later to round out the coverage.
Another lesson learned, is that, depending, it may be best to have the producer on site, either at a spot with wifi or using a mobile hotspot, so that the reporter can just drop off or quickly upload to the laptop the elements they have and then go back out to collect more (rather than have to sit down themselves, set up the internet connection, upload to the computer and then upload online themselves).
A third lesson learned, is probably to resist the temptation to use many mediums when covering a moving event, like a march, solo. I probably would have been better off with just an audio recorder and camera (relatively quick upload times compared to video) and made better use of Twitter (unfortunately, my phone’s data service cut out at the time preventing many posts.)
I think our project as a whole, covering two events, would have been made more doable and possibly interesting if we narrowed the scope a little, and maybe just identified three-four questions to ask participants at each event and juxtaposed the two, rather than trying to actually cover the events themselves or trying to use it to substantively get into the debate over same sex marriage and gay couples, which I think would be better done not as a cover it live module.
Overall, it was a useful activity and one that I think came off fairly well given the difficulties of producing something like this for the first time, with definite lessons learned for the next one.
