I think $1500 to $2000 on a Kay that is properly set up is a reasonable way to get into DB and make sure you like it, that you'll stick with it, because if you don't, you can sell the Kay for what you've got in it. This is not true of a lot of other inexpensive DBs. If you spend $1500 on any bass that has to come to you on a truck, you have to assume it will need some kind of set up for a few hundred perhaps. Then, a year or two from now, if you decide to upgrade or get out of DB, you've got something that may be harder to sell than an inexpensive Kay. Why? Because if a newbie was really in the market for a 'new' starter instrument, companies like Upton and others make it pretty attractive to just spend the $$ and do it through them--they take credit cards, they take care of the shipping, etc. If you're the seller of one of these used instruments, it's just harder to recoup all of the $$ you put into it. This isn't so, in my experience, with a Kay or the like....people just want 'em, and they'll pay for them and feel good about it.
In your exact spot, after playing a lot of instruments in that range, I decided to spend a little more--about $3k--and get something that was quite a bit nicer. It was carved and my teacher was impressed. So, make you sure you play some basses just outside your price range and see if you want to stretch a little. Having a teacher with you to help you make the call is also a good idea.
Neal