Here's what I would do, if it was me, and I had $2000 to spend. I'm specifically going for street kit here.
M3 single stroke, user condition. I've seen them go for under $600. User condition means bumps and scrapes and possible covering imperfections, but mechanically sound. A camera that wouldn't draw too much attention around here.
A Zeiss Opton Sonnar. I like the look of this lens quite a bit on my Kiev, and I highly doubt that I'd like any other lens better on my M. Very little flare, good color rendition, and fast enough to handle the toughest situations. I think the only thing that could replace it is the Cosina Voigtlander 50mm Nokton. But it just doesn't look the same. Both of these would need screwmount to M adapters, but that isn't a problem.
These things, if found in the right condition and the right price range, would cost me anywhere from $900-$1100 depending on market. That would leave me a decent chunk to spend on other glass. The question here would be whether to spend it all on a super fast wide angle lens or buy two slower lenses, one wide and one tele.
If I was going for the one wide, I'd probably go for a 35mm Nokton. It's huge, it blocks the viewfinder, but the speed is there when you need it. There's always using an external viewfinder with it if you have trouble composing. Look at shots with this lens wide open and you'll see that it does well in those conditions. It's a good lens for street shooting at night or in the occasional dark bar.
The other route, which would end up allowing more glass and more options, is the route of the slower glass. A 35/1.7 Ultron and a 90/3.5 APO-Lanthar. The 1.7 is still respectable enough in low light, and if you're as steady as I am with a camera you'll do fine in almost any situation. The Lanthar rounds out and makes this setup truly a kit.
I'd most likely have just enough money left over to get the screw to M adapters and some film to go with my new kit.
YMMV. This is just an idea.