We've done it a couple times.
I drew an Elk tag I'd be wanting and my hunting partner drew a Buck tag he'd been wanting in the same state.
We filled the time in between with an OTC tag in a bordering state. It worked out really well. I'd call that lucky though.
We also did a 27 day "Tour" years ago (before wives and kids). That was an absolute blast. However, it was tight on time.
All OTC tags except 1 draw tag he had for Deer.
We didn't give ourselves enough time to hit a hotel or anything. We were in tents or the truck for over 3 weeks.
We were whooped when it was over. The push to "get it done and get on the road" was always looming.
Meat care was also an issue. We learned some tricks on that trip.