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It's a little hard for me to take this critter seriously but who knows?   The trucks are real, so is the coupler pockets and some of the railings and grabs but the rest looks like fantasy land to me.   That diamond pattern is Christmas lights.   Someone better versed in the narrow gauge of Oregon needs to check this out.   Just south of Trinidad.
Probably West Side Lumber Co., maybe #6 says Roger Kirkpatrick.

It is one of the ex Westside Lumber Company 36" gauge caboose cars with extra windows, etc added (don't know which WSLCo number)...   To the best of my knowledge they were always 8-wheeled (bogie) crummies which takes them out of my definition of "Bobber" (4-wheeled, fixed)...   Cordially... John Campbell

I was talking to someone last night and we discussed these posts.   This person said almost for sure it is not ex WSL.   For one thing, we know where they all are or were.   All the WSL's had one window or none per side, and none on the ends.   That's a lot of trouble to go to for a little hack for display purposes.   And those end rails are ugly.   I woundn't be surprised to see that it's a replica.   Towle Bros. # 1 was built up from a flat car, and then virtually completely re-wooded in Auburn between 1959 and 1964 before being put on display.   It's not that hard.

Appreciate another perspective, but I'll stick with the WSLCo analysis...
A good candidate for the Trinidad, CA caboose would be WSLCo #6 which started out as #4 (1st) during 1941 and was assigned to the "Woods Roster" until circa 1944/45 when it was reassigned to "Work Train Service"...   and then renumbered #6 (circa 1950?)...   Was involved in a wreck during the 1950's resulting in one side being resided and was then returned to the "Woods Roster" where it stayed till the end of WSLCo operations...   Later it was reported as going to the Cumbres & Toltec Scenic, but I've not heard that it actually arrived there and subsequent visits to C&TS never found evidence it did...   At which point it went off of my radar...
The amount of alterations which the Trinidad, CA caboose has received are generally less common, but certainly not unique... Unfortunately ...  Cordially... John Campbell