So, I once submitted an idea much like this but reworked it;
A guildmaster foig offers jobs to the number of rogue levels the character has. I'd go for 5. 10. 20. 30. (30 would been epic if you'd have to sneak into Cordor castle)
These jobs are heavily pointed towards rogue skills and less so towards combat.
Steal x from location y;
Like a house, you will enter and deal with traps, sneaking past guards, deal with locks etc.
After each completion the player gains a choice reward "special item for rogue" or cold hard coin.