None of the advices worked so far using the Toyota 7. Guess a win is generated randomly as my AIs (5 so far) won certain events pretty easy where others struggled
You are babysitting your Bob right, and not pushing him like all the time?
I went the Toyota route and came back to these races, and found A-Spec no problem at all. Note you can use soft slicks in A-Spec, I didn't need any other mods though I did use ASM and anti-skid i admit, will go back and try without them later. Found the car a nice enough drive, have driven far worse.
B-Spec, Deep Forest wasn't too tricky with these settings but for Monaco I had to get the Stage 3 Turbo and rigidity mod. Also oil change each attempt but didn't pay out for overhaul engine/restore rigidity. I tried with the Stage 2 turbo but there would always be a 2J who got out front I could never quite overtake.
When I had the Stage 3 turbo for some reason the 2J driver seem to make more errors, he went out front but clipped something and spun around allowing me to take him early on, leaving me in second place behind a Jag, who was pretty easy to then reel in.
First couple of laps are often messy though, cars all over the place and Bob seems very cautious. Let the pack spread just a little, don't push him if you can help it (or unless his mood turns blue) and then if you come out of a corner into one of the straightish sections such as the uphill at the start or the tunnel, use overtake, but not when you are right up to the bumper of the car in front as Bob gets the shakes again, click when there is a gap of a few car lengths and he should dive past eventually. Sometimes the car you overtook will come out of the next corner faster and take you back, and Bob might just watch, so pace up now and then to prevent this.
Personally I never use pace down, but unlike some races where it seems to work, constantly hitting pace up in this race isn't a great plan and doesn't so much lead to errors as erratic use of the throttle and over-cautiousness. Let Bob chill and he will drive smoothly and reel people in.
Oh and I did try altering the tranny by reducing the max speed two clicks but then put it back to 199mph (with the turbo) and found this worked better. Didn't mess with any other settings, i'm sure some of the suggestions will help even more though.