Oldtimers, Youngtimers and Vintage Motoring

Hi guys, I recently took a trip to Italy to see my friend who purchased a 1997 Mercedes about a year ago, which is extremely comfortable and pretty reliable - he swears by it. We got into a chat about advantages, reliability and comfort of the older over newer cars and he got me kinda excited to get into classic motoring. I currently have a 2017 Honda Civic for which I pay a pretty penny every month (its a lease) and my contract runs out in two years. I started looking around for a classic alternative I could maybe get outright cash in hand or with a little help from a financing company. I see a lot of Jaguars XF and X-Type on the streets of UK, I looked them up on autotrader and they can go for anything from about 2k to 10k depending on the milage etc. - still about 5k less than price sticker of my Civic. So here is the question - is it worth looking into? What models/makes I could look into? What should I be aware of? Any tips? Tricks? I'm looking to expand my family in the coming years so a 3 doors sports car are out of the question :) Thanks