I'm no expert and there's a lot I don't really understand about it yet, but B-spec is going pretty well for me so far. Here are my thoughts from my own experiences - hope they're useful to someone, but don't take them as a definitive guide!
Pick the right driver - I went with the first option for my first driver, but found him so frustrating that I hired a second as soon as I could (B-spec level 5). My second driver has similar starting stats to the first, but has an ice cold temperament. This seems to be important when they have little skill - although he's in the red for most races he makes fewer mistakes, and at level 2 was winning races my original driver couldn't podium in at level 5, in the same cars.
Understand the commands - Increase and decrease pace are a little misleading. Although that's often their effect they actually seem to mean "try harder" and "calm down". Most of us have learned in our own driving that trying too hard leads to mistakes, and the same goes for B-spec Bob. If he's going off track or hanging out the back end of a RWD then you need to tell him to slow down, and if he's not using every inch of the track at the most demanding part of the lap you need to tell him to get a move on.
Pace commands last longer than the command timer - At first I thought that once the up arrow faded off the command button my driver would stop trying to drive fast and revert to his normal pace, so I spammed it at every chance. This doesn't seem to be the case - once you tell him to drive faster he'll try to keep driving at the new pace. Likewise if you tell him to slow down for a section he struggles with (eg first corner at London) he'll stay slow until you tell him to speed up again.
Don't overdo the overtaking - If you get the pacing right your driver can go from the back to the front of the field without a single overtake command from you. The command seems to tell him to really take risks to get past the car in front. I'm naturally cautious so I prefer not to use this at all. If you do want to use it, try to avoid it just before sections of track that your driver struggles with.
Pick the right car - Your driver will probably need a better car than you do - he's a genuine level 1 at the beginning, and most of us here haven't been that for a long time - but he should be able to win in a car that is close to the strongest AI cars. He will struggle, like many beginners, if you give him a car that's too demanding for the circuit or his abilities. I sent out a driver to try to win the AR Mini leg of the Sunday Cup in a RWD R32 Skyline, which resulted in a lot of driving sideways or across the grass - he won the same race easily in a much less powerful FWD car.
Hopefully that should help people get Bob off to winning ways!