Welcome Tom
I like your attitude

Not sure what to answer on which to buy... A "sorted" older car might be more of a known quantity than a brand new one. In the end some decent breakdown insurance will be the only peace of mind I think.
Will it be your only car? Just wondering what you will do if it snows... The rear wheel doesn't follow the tracks made by other cars....
I hope you go for it, looking forward to reading about it