Is it a license issue when it comes to different paint schemes? I'm hoping whenever Cane Creek is released the UP American flag scheme is an option.
What paint schemes DTG can use in a route is up to whoever they get the license from for the train. Examples are GWR only let DTG use the GWR green scheme, and in the new TGV route, SNCF only let DTG use the pink scheme.
In the case of UP I doubt it's much of a factor, Wasatch Grade and the SD70ACe Heritage packs both make use of their branding and several fallen flags they own without issue. I believe the only thing that would stop them from doing multiple liveries is time and resources. On that note my guess is that they'll only do one livery per loco, the AC44 will probably get the American Flag scheme as in general that's what is mostly used on most of the wide cab units these days, it's also what Sherman Hill used.
I think with the option of selecting a livery at least 2 of Union Pacific AC4400CW paints schemes "Should" be use. The current "Building America", with the lighting bolt scheme, and the older more basic one (They are still a very common scheme out on the west coast here) Building America Scheme Older Livery Hybrid Livery (Wings logo, lighting bolt scheme, no Building America flag or text) I also don't think UP has a problem with their older paints being put in game, but I don't think they will allow patched units (IE SP or CNW patched units)