I am halfway through 1999 without using any kind of special tips or even upgrades using Gear Head (actually very useful) Winter Shield and Head Master (got all randomly) It isn't that bad, and so far the actual harder parts have had very forgiving checkpoints, letting me start from there and save money at the beginning. It isn't "easy" but there is no reason to be intimidated by it. in fact so far, the hardest part for me has been before I got the shield at the very beginning of the game.
100+ Retail Games_100%
100,000 GS (9/12/09)
200,000 GS (2/2/2014) (I blame MMOs)