CUFANS,
Thinking more on the subject, I would go with the Trailer behind the 5er and use a Tire pressure monitor set up in the TV to keep an eye on the Cycle Trailers pressure. That was my only big concern regarding trailers behind 5ers. I have no experience with these Pressure Sensors but I believe some of our members have reported good things about them. They use them in their 5er wheels, but why not put one in the M/C Trailers wheel?
In case you haven't seen this,
http://cruiserlift.com/products.htm
Happy Camping