Doing this before the OM PEN dropped is tough!

Get an Olympus camera for EDC at any budget under $1k, size and features are just the best, tons of lenses too.

Picked up my x-t2 body for $400 a few years ago. Still going strong! Love the more compact prime lenses like 18mm f2, 23mm f2 and 35mm f2

Great video. I use my Nikon D5500 and Nikon D5600 for street photography.

I thinks it’s important to mention that especially with the Sony emount cameras  is that it is so easy to adapt vintage lenses with the systems.  Old glass can be gotten for little $$ though you’ll likely have to settle for manual focusing.  Some great old lenses and looks.

I bought a used Fujifilm X-E3 for ~450 EUR used in Japan. It was rated AB, but frankly by Western standards it is like new. Also got a brand new 27mm pancake for ~300 EUR. I consider this as a pretty good deal.

I’m gonna be sharing this video with so many people, this is super helpful!

Good topic, thanks!  I haven't done any purposeful street photography but I know the GX85 we have would work well, as it does for most everything. It is one thing I want to do more of.

Correction of a minor error: The original 6mp Canon Digital Rebel 300D does not use SD cards. It uses CompactFlash. But it produces very nice images and is one I prefer over later Canon DSLRs in spite of the tiny LCD screen.

MFT lover here! So good to use especially when travelling as it is small and pocketable. I have the Lumix GX1 and EPL6 from Japan paired with manual focus lenses for the retro vibe, and I don't mind the software 😅

Alternative to the D70 if you're on a budget : the D50 ! Same camera, one less dial in the front, but using SD cards instead of CF

I had the original Canon Rebel and it has a compact flash slot.

It's worth noting that if you're willing to wait/risk, you can likely snag some of these at significantly less. I picked up a boxed EPL-7 with kit zoom, flash, in the box and barely used for 120 euros last month. I have a Fujifilm X-E2 + a viltrox pancake 28mm and a Fuji 15-45mm zoom that cost me 300 all in. There's really great deals out there, they just don't hang around so keep your eyes peeled and you can snag them!

Equally, my best tip is buying gear bundles. People clearing out multiple bodies, multiple lenses etc and selling for a good price to clear everything out. I've gotten a lot of gear for free or at a slight profit this way, by selling what I don't want out of said bundle individually.

It's worth noting that some modern 3rd party lenses have trouble with autofocus on Nex and a5000 cameras. For example the Viltrox 28mm f4.5 cannot focus on my Nex 5. Only around the a6000 can you just buy lenses without checking compatibility charts.

The D200 has legendary color. What it's going for is probably fair.

M43:

For budget, I'd recommend the GF9 or GF10 (look up all the aliases for these two when searching!). They're the same camera, only the GF10 has this grip bar thing on the front. Just get the cheapest. It has the same sensor and, basically, the same firmware/menus as my top pick if you have the money for it. They even have a flip-up screen.

More expensive: Anything with an EVF. The Pen F is absolutely awesome! Then new OM System Pen F is probably awesome too. But the cutest and most impressive, considering it's even smaller then the GF9/GF10, is the GM5.

Weird choice camera, but capable stills: GF1. It's old and only does 720p vids, but the stills are great. And has most of the usual "creative filters", e.t.c.. Also, there's an optional EVF if you absolutely need one, but it's a bit low res. It does flip up, though.

Lenses: You mentioned the 20mm and the 14mm. That's basically as good as it gets for tiny primes! Very nice!

Some "fun" lenses to add that don't break the bank: Olympus 9mm body cap fisheye, and the M43 mount Holga.

MPB is great but I go eBay. Bought my Fujifilm X-T2 for $580 (body only) with a FX10-24 F4 and FX35 F2 and it all cost me $1,100 taxes included. I tend to source Japanese cameras and lenses because their condition standards are much higher than what’s in the United States.

Olympus EM5

Smaller lighter newer feature packed cameras are are nice but expensive. Since I could not afford such toys just for hobby I bought a D750, a 28-85AF-D, a 70-210 f/4 AF-D, a 50mm f/1.4G all together for less than 350 euros. Not compact, not light, but cheap and good IQ. Too heavy to carry them all, generally I choose just one lens and the camera for a day or place and got used with that compromise.
But I can't deny, I would like a mirrorless APSC or FF together with 2 pancakes. But don't like the idea of going around all day with a 1000 euros hanging off my neck. Probably if you're that rich to consider a 1000 euros an expendable setup, that's the right one for you.

At this point, having a budget of a grand. Just go Sony, and get chinese prime lenses and you're good. Even in the lower budget, getting the a5000 plus aps-c viltrox lens is a better choice. Having more lens option is the key. I won't recommend the dslr route if you plan on getting more lenses with newer designs. DSLRs are for getting that nostalgic feel and the use of the OVF, but if you aim to learn and progress, E-mount is the way to go.