I shoot a BEATER M2. I got it for $400. This can happen. It's vulcanite is half gone (I'm going to replace it with a piece of salmon leather I have) and it has somebody's driver's license number crudely inscribed on the top with one of those vibrating engravers. Mechanically, it seems to be perfect. My M5, which LOOKS perfect, needs CLA, the shutter curtains are unbalanced above 1/50, which is going to cost at least $250. The lens I am using (I have others, but this usually stays on) is a CV 40mm f/1.4, the single coated version that was made for the Japanese market. I got it on ebay for about $350, can't remember exactly offhand. The lens is perfect, really brand new, but has been modified to bring up the 35mm frame lines rather than the 50mm. I happen to like the perspective, and I don't like to have to make decisions about lenses and fumble around for the one I want; so I've drawn that limit for myself, mostly. The lens is superb. I guess my former dr summicron 50 was sharper, but actually, I never notice anything wrong with this one.
So I guess that gives me about a $750 camera. I already had a light meter, but having to carry it is an issue, for sure.
I started with a loaner M5 in 1975, and I have a special fondness for the camera, though there are others who despise it. That's their problem. It is a great camera with a great meter; it just got a bad rap by users who were expecting an M3 with a meter, which they didn't get. Instead, they got a very advanced camera that really should have met a LOT more success. Because they are not universally sought as the M6, MP, M7 might be, they tend to go for significantly less $$. They are a bit larger, a bit heavier, and have a more square aspect.
The CL idea is a good one, but remember, if you are looking for a LEICA, the CL was a partnership with Minolta, much like the recent partnership agreement with Panasonic for some of the digital cameras. The camera was built in Japan. I don't know if this is important to you, but it is to some people. Some think it is not as well built. Another potential drawback is that the rangefinder base is significantly shorter, since the camera's size requires that. Check Wikipedia, or other reference source. I really doubt that a CL would survive hitting the earth at terminal velocity, having dropped out of an airplane, as many M2's and 3's were known to have. One great thing about my M2 is the confidence I have that if someone tries to take it away from me (unlikely because it's so ugly) I can just hit him with it. The camera won't break, but his skull might.
Like a previous poster, I have not found a pocket camera practical, so I strap it. This is actually an advantage on the street because you are known to be a photographer, and upsetting people by surprising them is much less likely.
I shot with another M2 and an M4 for many years, for my living, shooting travel stories for a magazine. I just don't feel right with anything else. That's the risk you run. Leicas ARE ADDICTIVE. The nice thing is that no matter how ugly your Leica might be, as long as it is mechanically right, it is still a Leica. Nobody will be able to see how ugly the camera is by looking at the pictures.