The most annoying part of the process is being required to download CSV files from each of my bank/cc/investment accounts.
I thought about building some APIs to be able to download this data automatically but some of my banks do not have publicly available APIs. That's hilarious to me because something like Mint or Plaid can get API access to my bank transactions but I, the owner the of the accounts, cannot.
Not only that, but you can only download CSVs for the last 2 years. Mint/Plaid can get the entire account history.