if I have a wallet with 100$ and I sent out about 90ish transactions from said wallet, could someone check the ledger and identify said transactions came from the same source?
Wallet balance is a collection of all balances with all addresses (UTXO) that were listed in previous blocks, so if you do not control how to send your money and how to control your privacy, your transactions will be tracked.
One way to increase security is to use a well-programmed wallet that supports coin control.