What Trailer did you end up buying, I'm looking at doing something similar

Thanks

Any update and pics to share?

you may also look into fitting electric brakes to the trailer, similar to those fitted on larger trailers.
The have an adjustable control unit and are switched by the stop light. Your braking would be better controlled, not to mention safer.
They would take a little to get used to, however the safety factor far out weighs the training time needed,,,,,,,,

a sportster will pull a trailer fine, but your fuel economy will suffeer so budget for more fuel. 

the TWO big issues as far as im concerned, and ive towed trailers thousands of Ks behind bikes, are

 

 A) TYRE RATING ON SMALL TRAILERS.. some of those small tyres you see on micro trailers are not highway speed rated, and one of the last things you need out the back of nowhere is a tyre issue... also if its a second hand trailer it may wel have sat unused for some time and the tyres which are poorly rated will also be semi perished... so check the rating, and check the age..

B) WHEEL BEARING AND SPINDLE... again you may find poor quality bearings that arent up for the long haul.. when running a small circumfrence tyre that bearing is spinning quite fast and a long trip may be the death od your bearings.

If you havent got a trailer yet these are things th look out for... you nay find good wheels and bearings on a small trailer.. shit a mini cooper s has been running 10 inch wheels at 120 mph for years, but not on crap bearings.

if you use a small wheller i would replace the tyres and bearings and get good grease b4 the ride.

hope this helps