Upload & Sell: On
you're looking for Leica R slr lenses, not the current production M mount rangefinder lenses.
1000 dollars does get you a 60/2.8 macro elmarit and a not so wide Leica R lens, or a 50/2 zuiko macro and an 18/3.5.
I think if the budget is only $1,000 It certainly would rule out Leica R as even the older 19mm f/2.8 typically sells for about $900.
Unfortunately unless you are very patient and find very good deals it also rules out Olympus OM. I think the 18 f/3.5 sells for about $750 and the 50 f/2 macro for about $400. So they would work with a stretch of the budget, but not otherwise.
My suggestion would be Canon FD. See the thread that Fred started on the 20 f/2.8. It looks like it is quite workable and goes for around $300. You could also get an FD 200 f/4 macro, that is supposed to be quite nice for about $500.
If you could stretch the budget, however, the Olys might be better. It might also be worth consider the Contax/Yashica mount Zeiss. The 18 f/4 has it weaknesses, but the 100 f/2.8 macro is very nice and they would be just over $1,000 as well.
Another strategy might be to get a ZF 18mm f/3.5 and an inexpensive Nikon Micro which would use the same adapter. There are some real bargains in the Nikon Micros. If you need to hold the line on the budget a Nikon 55 f/3.5 AiS and the ZF 18 will keep you under $1,000 but you should be able to get the Nikon 105 f/2.8 micro for about $250 and you might like the longer focal length. Most macro lenses are very good and these two may not stand out as macro lenses, but they are very good and will keep you in budget.