Welcome to the Forum .
I can relate a little with you . I to work as somewhat in the IT field. And I have worked at a dealer for abut 6 to 7 years as a Tech. Now I wrench on sleds in my spare time. Up until last year I had an 1996 XLT . Last year i bought an 2013 Indy . This year i bought an 2005 IQ Racer for the wife . The sled was in horrible shape (thought about junking it ) however it was a real fun summer project.
My advice Do it ... The 440 was a great sled easy on gas lots of power for the cc and very tough. I wouldn't think twice. This forum is great for help and if you need anything pm me or post in the forum. I might even have the shop manual for it .