Sam_W Offline Upload & Sell: Off
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This one is a thorny question, partially because of the price cap (assuming US$500), and because that 3D pop is dependent on not just the lens' microcontrast/coatings/age, but also your shooting style and to a certain extent the sensor of the body.
Setting aside the latter bits, there's two categories to look at:
1. The more modern ZE/ZF.2 (or even Milvus if priced cheaply enough): I would generally avoid the Planars, except the Makro-Planar 2/50, which was pretty fantastic all-around, and had good micro contrast and pop. It's just often not below $500. The Distagon 2/35 is definitely good for 3D pop. The 28/2 and 25/8 (also, depending, the 2.8/25) Distagons are great, depending on your preference and how good of a deal you get. Note that you won't get consistent results with them, they have specific "zones" and styles in which they produce great 3D pop, vs just average lens performance. It'll be a learning experience to figure out the sweet spots.
2. The older C/Y lenses, which can often be had for a steal. You'll want to aim for the modern MMJ ones, as they'll have better/improved coatings, which help with microcontrast. Also, generally aim for serial numbers in the late 7mil or low 8mil. Good ones are the Distagon 2.8/28, which just delivers, and is super cheap. The 2.8/35 is pretty good, too, though not necessarily inspiring. While way out of your price range, even beat up, the Distagon 2.8/21 C/Y is fantastic for 3D pop and microcontrast. An important bit is roughly when the lens was designed - if it's late 80s to early 90s, you'll do well, but only a few were designed or updated during that time.
3. The probably-more-expensive-but-interesting area is the G lenses, which require a rehousing to get a mount change from Contax G (autofocus rangefinder) to something like Leica M, which you then further adapt to your R mount. Most of these are newer designs, have modern (as of the 90s) coatings, and can be found quite cheaply. You can even do the rehousing yourself via kits you buy with instructions, because you're basically popping out the entire lens assembly into a new helicoid.
Just some thoughts, probably ending up more confused by the end!
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