You have no idea how much your title pleases me. Short and concise, as a title should. Anyway, I think I'm at around 75. Sweep and Bedlam in the same hold is probably the most efficient way, but numbers and heist in the same shop would also be quite fast.
I'm somewhere above 75 in the number I jobs I've done. I recently hit 1,000,000 gold. The Thieves Guild questline is most definitely my favorite, especially since there's still a lot to do after you finish it.
(I think I have the keys for almost every house in Skyrim...)
Shill and Numbers jobs are the fastest and easiest. Quick money for the 100,000 gold achievement, and gets the One with the Shadows achievement the quickest too. I'm doing my fourth Skyrim achievement run on Master on a third account. If you have any questions about the game, just ask. I'm doing a Legendary acheivement run next.
If you're sick to death of the radiant quests and want to skip right to 125 jobs, simply use console command "set TGRMasterTotal to 125". To confirm this has worked, follow-up by using console command "show TGRMasterTotal".
Note to above: If you want all the interim trophies and not just the safe at the end, use "set TGRMasterTotal to #" to get just below the next achievement and then carry out one job to get the trophy for that increment e.g. say "show TGRMasterTotal" returns number "32", simply "set TGRMasterTotal to 34" and carry out one more job to get the trophy for doing 35 jobs, and continue the same way until set to 124 and do final job for the replenishing safe.