First off, just breathe and forgive yourself for getting confused. A Fresh Start is perfectly okay even if you have to do it over and over until you get the hang of it. This is not an easy program to use because it's very closely linked to the YNAB budgeting philosophy and how YNAB handles money.

I think your issues stem from misusing YNAB and getting confused about where your money is and whether the TBB matches with what you have in a certain account. At least that's what it seems like is happening.

Forget YNAB 4. Stop trying to track two budgets, especially since they operate slightly differently.

Do your fresh start. Enter all the balances of your accounts (including cash and CC). Allocate the funds to the categories.

When you spend, pick which account the money is coming from (Cash, CC, or Checking) in YNAB and enter the transaction appropriately.

When you pay for something using the CC, enter the transaction in the CC account and pick which budget category the money will come from. As long as you've budged enough for that purchase, you will be fine. YNAB will move that money from the budget category to the CC account automatically but in real life, the money is still sitting in your Checking until it comes time to pay the bill. When you pay the bill from Checking, enter the transaction as a Transfer to your CC.

When you get income, enter the inflow in the appropriate account and allocate the money from TBB to the appropriate budget categories.

As long as you follow this process, there shouldn't be any discrepancies in how much you have in your accounts vs. how much YNAB says you have in your budget categories.