I'd go for a 'chain' medium hobo with horsebit detail strap ($850). I purchased a D-gold hobo as my first
Gucci bag and sort of regret it. The circular shoulder strap is not too comfortable on your shoulder after a while, as it digs into your shoulder. I don't even have many items in my bag to weigh it down that much. I've posted about my complaints before -- another thing is that where the strap meets the gold ring to attach to the bag, the threads begin to frey. So I brought it back to Gucci and they sent it out for repair saying that they could seal the area so it wouldn't happen again...... I get it back, and it is in better condition... but still freying. Looks like they just trimmed the threads. All in all, I'd say throw in a little more and get a horsebit hobo instead.
I wish I had purchased the horsebit hobo instead as my first bag............