I had a hugabub and loved it while DD was small (up to about 18lbs, when it really started to struggle). It's longer than my Didymos 7, but tapered towards the ends so you don't wind up drowning in fabric. I liked the way it all folds into the pocket for easy storage when you get back to the car. I found the stretchiness made the learning curve much easier when DD and I were both getting to grips with slinging - there's a lot more tolerance in how you tie it before you run into safety problems.
To be honest, I suspect there isn't that much difference in useability between the stretchy wraps - I don't think I've seen any threads where anyone hasn't loved whichever stretchy wrap they got.
My experience is that the weight of the sling isn't necessarily an issue when it comes to supportiveness - DD is now 18 months and about 25lb, and I find my Didy Indio (cotton) more wearable than a friends wool mix didy. The wool mix is thicker, but that also makes it bulkier - my shoulders are quite narrow and its not a good combination... The wool mix is also noticeably warmer (which wasn't really an issue this year, but if you go on holiday or we ever get a decent summer it might be).
Have you come across www.slingmeet.co.uk/? If you can find people local to you you could probably arrange to try a few options (or at least have a prod and a poke) before you buy.
My hugabub has definitly done me a good turn, but I don't think it would be up to another baby. Woven wraps, however, go on and on and on and are well worth looking for 2nd hand.
Oh - and as for splashing out on slings, I've now got the Hugabub (held onto cos I'm sentimental ), the Didy and 3 Mei Tais. And I'm half looking for a shorter Didy to do rucks with. They can get addictive...