Most skidder work I have seen is rarely on hard footing. I know the proper way would be to match up closer, but to get by when it is what you have, watch out for binding. If it is not binding up I would say it would be OK. Traveling long distances in one direction with no slippage will likely cause problems, buy if there is some tire slip in soft ground you will probably be OK.
I am assuming it is 4 wheel drive.
If you have a temp gun you can shoot the output shaft bearing areas in the t-case. If it is binding, it will be hotter than normal. If not, no problem.
Remember if you go to hard ground it will be a bigger problem.
Hope this helps.
Any picture of the machine?