Old Money is a big plus, but remember in the Early part of the 1920's and in the 1910's and before, big wide dollar bills called "horse blankets" were used. Then new narrow bills came out in the latter part of the 1920's. So you could visit 1929 before the stock market crash, but remember there are few jobs in the 1930's due to the great depression.
The best jobs to get in the 1920's were jobs that paid tips like busboy or bellboy. Most high paying jobs like factory worker require ID. Still it was easy back then to get a job in a restaurant as a busboy.
Most people back then did not go to college and trades were popular, like radio repairman or auto mechanic. It was rare for people to carry big bills like 50's & 100's. The nickelodeon (cinema) was just a nickel and a bottle of coke was a nickel and a candy bar was a nickel. They used buffalo nickels back then, so having a few is a good idea.
The most important thing to keep in mind is that different timelines have different rules. On some guns are illegal, on others you need a special license, on yet others you are on your own.
A good idea is to have period clothes and to look "normal" and if possible a bit drab and boring. You do not want to stand out in a crowd, but to blend in.
Flashing big bills is a way to attract a lot of unwanted attention to your own self. Steven Gibbs says that paper crumbles after a few days on the other side, so it might be a good idea to change your money.
