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Let me qualify again by saying I am NOT an expert by any means. I have upgraded from ProX to D132.

Regarding Questions #1 and #2. Not sure. The newer Evolution (analogue) cars come with plugs so you do not have to solder anything - just purchase the correct digital board (there are a couple options) and they literally just plug in (i got Digital 132 boards for $17USD). I believe in older cars it is theoretically possible - however you might have to drill a hole and solder a little as well as figure out how to hold the digital board in place (hot glue would probably work for that).

I believe most if not all of your track should work. All turns and straights and the chicane and even the crossover should all work.

Regarding track - digital probably requires better electrical connections and you probably would notice dead spots more in digital than you would in analogue. So clean your track - and you might want to add Power Taps if you have a larger layout. I only have Carrera and have not experienced any track problems - and I have heard that Carrera track is the most reliable. But, I have no way of testing that.