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As a trained pilot, flight planning is a huge part of your job.

Navigation is also a big part of the job. if you assumed you had to turn off parts of your nav equipment to avoid detection, then visual reference (ie flying the path to visually memorise/familirise yourself with wayppoints) would be something you'd certainly do - and a flightsim would be perfect for this.

was the terrain modeling good enough at that time to really train you for that? Current MSFS sure but the version he was running?

Sure. Flight Simulator X came out around 2006 and at max settings looked great. Current FS is obviously better, but FSX was adequate.

I couldn't fly seriously in a flight sim, I'd get bored quickly and do a loop or dramatic crashes, lol.

I mean I'd still like to try out the new MS Flight Simulator because it's impressive technology.

Miegs field. Cessna 172. Enable slew mode.

Flight Sim 95? Outstanding.