I've been running roulette betting systems through a simulator, 10,000 simulated players per system and goal, single-zero wheel. Each player stops when they hit the goal or can't cover the next bet. One result surprised me more than any single system: the "best" system changes completely with the goal.
Small goal: win $50 and walk away
Martingale on red with $2,550 (8 doublings from $10): about 97–98% of players get there.
The mathematical ceiling for that bankroll and goal is about 97.7% (Bold Play, Dubins & Savage). So Martingale is almost perfect for this.
Most progression systems land 2–6 points below the ceiling.
Big goal: double the bankroll
Same Martingale, same $2,550: only about 1 player in 3 doubles it.
The ceiling for doubling is 48.6%, whatever the bankroll.
Putting everything on red, once, hits 48.6% exactly. The "dumbest" bet in the book is the best possible play.
Grinders like Oscar's Grind and D'Alembert, which look great at +$50, fall to roughly 25–30%.
Why
Every spin costs you 2.7% of what you bet. A small goal ends in a few spins, so a system that wins small and often is close to optimal. A big goal takes hundreds of spins with Martingale or Oscar's Grind, and the house edge grinds the bankroll down long before the target. The single bet gives the edge exactly one chance.
What it means
There is no "best roulette system", only the best one for the goal you set. And the bigger the goal, the more a plain bold bet beats every clever progression.
Full disclosure: I built the simulator myself. No link here, I'm only interested in the discussion.
Questions for you: What goal do you usually set when you sit down? And does anyone play a system that is meant for big goals? I'm happy to run it through the same test and post the numbers here.

