These are nice ideas, but why not just plan your town stops?
When back in the 1800's and I was a younger man =)
I never pitched the tent. Always under the stars.
If I pitched my tent I may aswell have shouted at the top of my voice,
I HAVE MONEY, COME ROB ME!
NO, I only pitched tents when in convoy, and miles from the nearest town.
However...
My regulators and I often constructed small hunting cabins in the mountains.
Only we knew of their location, and they where well hidden.
They offered minimal rest, and served us well whilst we where tending the lands.
In reference to the thread "baccy don't grow here"
it was suggested we have certain resources for certain areas.
Having a hunting lodge near the main area for a particular resource,
is how my crew and I dealt with the vast travel.
ANIMALS? I used to use a hunting bird to locate a good spot for a lodge.
Location... Mountains and forests.
Marked on the map for my town only.
If a player looses a duel, maybe he reveals locations of lodges.
As always, open for a slating =D