You can go with a lower price rig and update it as the budget will allow (Like I did) Or look at what you might spend in updates and go with a newer rig.
My 1995 FLD120 has 500,000 and seemed to be in perfect condition. Just considering mechanical updates I probably easily have $10,000 wrapped up (new radiator, u-joints, front brakes, tires & rims, and a bunch of other little items). I also updated the interior and added chrome which racked up another $5,000.
I probably could have easily moved up to 1998 - 99 rig, but that could have had similiar updates required, you never know.
I am super happy with my truck now, and it runs and drives like new.
1995 FL FLD120, M11, custom interior.
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