Moving to a lithium ion build, need some help

So I built a electric longboard not too long ago, with 2 3c 5000mah lipos, dexter’s single motor kit, a 190kv motor as well as a QuicRun WP 8BL150 esc. There is a few things that I’m not to fond of. One being inconvenience. The lipos are a pain, a cheap well performing pain. The charging is what annoys me the most. I use my board as transportation, and fun of course. :wink: But when you have to discharge them when you are not using them for more that 48 hours and that 100-200 cycle count hurts. So I plan on moving to a lithium ion battery, a 36v 10a one. Not sure what needs to change in my setup for that to happen. Also the terrain where I live is rather harsh. (it’s one of those roads where there is just a bunch of pebbles infused together with some tar.) So the 83mm that dex has which I don’t know the “A” rating or whatever the terminology is, feels pretty rough.

Now the changes… I need some opinions on these changes though.

New deck, maybe blank full bamboo deck, that should help rough roads?

New wheels that can fit dexter’s motor kit, that have a low “A” rating for more smoothness

New battery, Lithium ion 36v 10. For more range. Can’t have too much range :wink: and whatever changes need to be made, assuming that the esc needs the change. But all the escs I looked for always have compatibly with how-ever-many cells of lipos and nimhs, but never say anything about lithium ions :’(

So if you guys can help me that would be fantastic. Cheers!