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I bought a 197 purely because I could, I work in the motor trade and got one cheap with even cheaper finance... it was rude not to at the time.
There were a few things I wasn't so keen on, like the ride height and the lack of torque... so addressed these issues with a remap and coilovers...
It's a difficult decision tbh, so many options! You're always going to lose money trading your car in, and if you start modding a diesel you'll start to lose the ecconomy. A 182 is great but with the miles you do you need something reasonably new with warranty.
I'd say drive a cup-pack diesel...