I do not have that loader but one similar on my 2320 (200cx). The loader is pretty strong and would fairly easily dig up shrubs, ground likely deeper than 2-3" and small trees. From what you describe, an H120 and 1026 should do similarly and adequately for your goals. The key IMO for the digging part is
ballast. The 1026 has a powerful engine but is fairly light so adding ballast both on wheels and hitch is essential to doing much ground engagement. Although on paper the 1026 and the 2320 seem similar, the 2320 is a much larger tractor and is heavier. I would count on adding 100-200 pounds on ON WHEEL ballast and probably 300+ pounds on hitch to be able to accomplish your tasks without difficulty. I would also investigate a tooth bar for your loader as it really helps digging up dirt and or greenery you want to move or extract. I do not know if there is one available for your loader yet or not, but you can always have one fabricated. Having run larger tractors than the one I have now, I can say you will be surprised by what your machine will be able to do. The loaders on the small 1000 and 2000 machines (except the 2520 and 2720) are slow relative to the 3000 series and up but they will lift a lot and perform just as well albeit on a smaller scale. I would argue for tight quarters such as making trails, they may be better than the larger tractors. There are many places I comfortably take my 2320 that I would have never taken my 3720 or my 4520 prior.
John M