I'm thinking 600lb bike but then the added weight of the trailer needs to factored in as well. I know some of the Aluma bike trailers are around 400lbs give or take. So, ballpark, you're looking at towing an estimated 1000lbs - once again give or take a little.
About the only refreshing thing about that is the lack of wind resistance...or at least not much wind resistance. Something to think about. If the trailer had a brakes...I would almost feel more comfortable towing the Smart with the Bike.
I have heard of the Trailer in a Bag which is a trailer that disassembles and can be put in a sack and thrown into a trunk.It is basically an axle with an I beam/tongue combination.It is supposed to be lightweight enough to be picked up by 1 person.This and a dresser should be about 1000 lbs.
Any touring or cruiser bike on a trailer is too much for a Smart. Easier to tow the Smart on a trailer behind the bike.... ;-)
JMHO
Check the GCVW and GVWR for the Smart and you'll see that there isn't much left when ya put two folks and a suitcase in the Smart. The tongue weight alone would probably put ya over gross. just a thunk
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2010 Smart 
1 - Kermit
3 - The Street Rod
4 - Split Window Vette
5 - The Veggie VW
smart - aka Smurf
I don't know what it weighs, but it is less than 1 inch shorter than a fortwo.
1 - LT N FLFY
2 - Forests ride
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