Welcome to the wonderful world of slightly larger tubeless tires. It didn't take me long to decide that there'd be no going back.
What sealant are you using? I'm surprised that they're losing more air than your tubed setup.
I haven't been able to get a set of Schwalbes to seat with a track pump and would recommend a flash charger if you don't want to buy a compressor. There are two ways to go about it: a) new pump with the charger built in b) secondary canister that you charge with your existing track pump. I'm doing the latter, a unit from Specialized. It's only okay, if I'm being honest. From what I've seen from tests online, my Spec model doesn't have the greatest volume/sec, so I'd encourage you to look online at some of the alternatives (I think that the Schwalbe canister is supposed to be decent). Getting a secondary canister is the less expensive option of the two.
You'll also continue to refine your technique as you go, so don't get too discouraged by the difficulty of mounting the first few times. The first time I mounted Schwalbes, it was a bear. The last few times have been easy peasy. The thing that helped me the most is utilizing the center channel in the rim bed, both for getting the tire on the rim and for seating the tire. Before attempting to seat, make sure the beads are in the middle, all the way around, and spray the rim bed/tape with slightly soapy water - it'll reduce the friction between the beads and the tape, making it a easier for the beads to pop up in to place.