Struggling to get accurate balances which match the bank
I have tried YNAB 3 times, and had to reset my budget 5 times as the budgets never seem to line up and after a month things are all out of wack. I just keep going back to a new budget each month and don't feel there is any value.
1 Checking, 1 Savings, 1 CC, 1 External Savings Account
I do have some automated transfers from my checking to the external account that is not included in YNAB but the others are. I can't get the TBB and other balances to match what I actually do in my accounts. I have things set to auto and tried manual, but it was way too much work. Any insight? I have done all the YNAB classes and watched all of the recommended YouTube videos on subjects.
Step 1 is to make sure the accounts match the real world. Record real-world transfers as transfers in YNAB; specify in the Payee field and no category is used. Import usually screws this up until you've edited a transaction and established a Payee Renaming rule.
Step 2 is to realize the budget is simply a shell game. Move funds wherever you like. This is your PLAN for future spending/saving. (Saving is merely delayed spending!)
TBB "should" be something -- the only value it should be is $0. If it's not, then budget until it is.
Some category "should" match some account -- this is a holdover from past budgeting practices and nothing in YNAB enforces this. Change your mindset to "categories define purpose" and "accounts hold dollars -- NOT specific categories".
It can take some getting used to. I never reconcile my account (probably should but I don't). Sometimes it gets out of sync if you are waiting for it to import instead of you putting in the transactions.
Sometimes transactions get messed up and transfer doesn't work as they should. I have a "Target" bucket (too lazy to break target out, I know I should) and I bought something there that cost more than I usually do so I put it under household as it was the only item, now every time I import they get marked as household instead of Target. I have to change it back and then it goes back to Target, it seems to take whatever the last one was when importing.
CC can be tricky. I don't use them as they say because it messes with my budget. So I can't help you there.
As @dakinemaui said, first get your YNAB checking and savings accounts to match the real accounts. Make sure every imported item has the appropriate category(ies) assigned to it, that all incoming funds (that aren't transfers from another on budget account) are categorized to TBB, that transfers between on-budget accounts have the Payee as "Transfer : (whatever account)". If you're just starting out you should pay close attention to every imported transaction and make sure it has all of the information how you want to see it in your budget.
Then on the web application you should try to reconcile those accounts. If they don't match don't click "No", exit Reconcile and go transaction by transaction comparing your "real" bank accounts with your YNAB bank accounts. Delete any duplicate transactions, etc. and try Reconcile again. With only a month or so's activity this should be fairly easy. (While doing this make sure you're starting balance is correct as well.)
As Periwinkle Flute says, you need to get the balances right FIRST. If you absolutely cannot get them to balance, reconcile and let YNAB enter an adjustment. You can fix it later if you figure it out.
I would also recommend putting the external account on the budget. What is it for? I did this a few months in and it made things much simpler.
As for entering, manual is the way to go. Especially in your case where you haven't got a full handle on what is happening. You can't have that many transactions. I think on my busiest day I might have 8 transactions. Most days its 1 or 2.
picture all the money in your accounts on the table. Now divide that into 3 piles. This should be the starting (current) balance in your accounts. At this point we haven't budgeted for anything yet (if you have, clear out all the available amounts). TBB should equal the total of the money.
Now decide what that money needs to be spent on. (added a note here about the external account. If you have that set up as saving for something, now that it is in the budget make sure you allocate that amount to a budget category). Generally food and shelter go first. So allocate (budget) some of the money there. Keep going through everything you spend money on in your life. Christmas, birthdays, commuting, haircuts, dog treats, etc. Keep putting money into the categories based on the next highest priority. For example, Christmas is coming. That is a higher priority than your friend's birthday in September.
Do this until one of 3 things happen.
1) TBB is at $0 but you haven't covered the essentials. This is super stressful. For some things, like food, you don't have to budget the whole month at once. Just worry about what has to happen until your next pay or inflow of money. Still short? Then you have to look at cutting some expenses or making some quick cash.
2) TBB is at $0 but you still have things that need budget dollars. Here you can decide to rearrange some priorities or set some goals to save up (for example, for your friends birthday in September).
3) TBB has money left and you have no more categories to budget to. YAY! That is awesome. Now you have to dream about what that money should do. Most YNABers will now get to a month ahead. I personally have a separate category for this and put the budget there. Others do it the YNAB way and budget into the future. Either way works. Once you are a month ahead, then you need to build an emergency fund. At least a couple of thousand dollars for stuff that happens or that you forgot. Then you get to dream. House? Car? Retirement?
Edited to add one more question - do you have a balance on the credit card? Any balance? Like if you went on the bank site today would you owe money? Then you need to have that entered (as a negative) and budget for the amount in full (if you pay your card in full). If you don't then you need to put in the amount you can afford to pay toward the balance.