a tubeless set up involves taking the inner tube out and using sealent in stead. Its described in this thread I've decided to go tubeless .
On a 36er inner tubes are incredibly heavy so significant weight reductions can be had by going tubeless but it is a very fiddly process. I’m not sure of the general benefits for doing it on a smaller wheel.
Hillclimbing ability on any uni depends on crank length and wheel weight. As fun as it can be, 36ers have very heavy wheelsets (my v2 has a wheel almost as heavy as an entire 29er). They run on inertia and feel incredibly fast and stable in the right conditions, however lots of hills is not really optimal territory for them. Unlike smaller unis i find that its best to dress like a cyclist on a 36 which may not be so good for a commute.
A 29er will not have problems with pretty much any hill with a road on it. Compared to a 36er they are very responsive, in fact they feel more like a 20 than a 36. What they are more similar to the 36er in is smoothness and rollover ability.