If it is in physically good shape (or even physically respectable shape) - I'd say that CDN$2000 was a fairly good deal.
One thing to look out for on Bolers however is a known weak spot in the frame. The frame elements running the length of the trailer bend inwards near the front. That bend is the weak spot and MANY Bolers will have a frame crack at that point. That being said - it's something to check (and maybe a nice bargaining chip) but there's little reason for it to be a deal breaker. It can be reinforced at pretty much any welding shop. We had ours done soon after we bought it for a cost of about US$130. However that figure also included the labor to weld on the four scissor jacks we had onto the frame too. The actual frame repair was pretty simple compared to that. :)
When it comes to the basic structural elements of the trailer (frame, floor, shell, seats, beds etc) there isn't much that isn't fairly easily repaired one way or another (I can direct you to the photos of mine during restoration if you're interested).
Frankly - working on a Boler
is gonna seem like childs play relative to the work I'm guessing was done on that '55 Chev.