There are two general kinds of entries that should be in the ledger:
A budget entry for any planned to spend money. Every time something gets approved it should get entered. This lets everyone see what is planned and how much money is left. You can also enter things that you think might get approved to "block" money for them. It is suggested that you the word "proposed" in their name or something similar to flag them. If they get approved, remove the word. If they don’t get approved, delete the entry (or comment it out).
A transaction entry for every actual spend of money. Ideally these are done as soon as possible after the money is spent. This will cause the budget created in step 1 to get reduced.
It is suggested that the work be divided to make it easier and not overload one person. For example, it is probably best for the budget entries (#1) to be made by the treasurer and the transaction entries (#2) to be made by the card holder (or the treasurer if a non-card transaction). It is also a reasonable and good idea to encourage any contributor to submit a PR with the entries for ticket approvals if you have that capacity.
The goal is to have accurate timely records that are easily maintained by a large group of people.
Swag is budgeted for (#1) and then purchased (#2). If your region buys swag in large quantities and then distributes it across multiple events, it is not necessary for the ledger files to show how much swag went to each event (unless that is useful for you). From a Fedora Project perspective we just need to know how much we budgeted for Swag and how much we spent.
It is also not necessary to break out bank fees like Paypal, however it is strongly encouraged that you do it. This will allow us to udit these fees and see if we can get some lower cost options where it is possible or alternatives from accounting. If you don’t want to break out those fees though, you are not required to do so.