Maybe 6 weeks ago I bought this saddle second-hand. It fits me and my horse great but I hate the high contrast two-tone look. I’ve been lightly oiling it basically after every use (3-5x/week) and made some progress, but I don’t want to go much more overboard and kill the leather. Any advice on an approach? Photos when I first bought it and now - I know lighting/angle isn’t consistent but it looks pretty true to life to me.
I think it looks nice the way it is. If you really want to change the color, check out this blog. She has several posts on different saddles she’s done.
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Agreed - that type of dye job will develop a rich patina with age and good conditioning, but it will always be two-tone contrast. If anything, the lighter will become more red as you condition. I have an Ainsley that has a similar dual-color contrast and it has darkened beautifully in the last 20 years – it is now almost a dark oxblood color on the lighter panels and dark havana on the seat. It will never not be two toned.
If you’re brave, go for the dye job… but one thing I realized after doing the dyeing journey myself (and I’m plenty happy with the end result!) is that you really need to do it on bone dry leather. If you conditioned it in the last few weeks, consider waiting a bit until you know that all the oil/conditioner under the surface is fully dissipated. What happened to me was after I dyed, the residual conditioner seeped to the surface because the dye seeped through the collagen fibers of the leather and pushed it out – this is totally natural and is how skin and leather works, but it resulted in me having to only use black breeches for a while.
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I’m not. Patience it is! 
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Looks nice just where you have it ! I’d stop here. You did a really nice ( not too much ) job !
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I think it looks nice, but if you do want to take it slightly darker, you could do a layer of hydrophane darkening oil. (Assuming you’ve just used regular oil so far.)
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I’d stop there, and also remember that on seats and knee rolls the leather is glued to the padding below. Lots of oil will weaken that glue and make it come apart, which is what you often see in those calf covered French saddles.
I have dyed a saddle twice, and was really happy with the results. As mentioned you do have to dry out the leather, and strip it using acetone before placing your dye on and letting it soak in, and then sealing it really thoroughly. It’s a messy process, do you want to wear gloves and do it outside, but I think it’s worth it.
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