RE: 1. Is it acceptable to enter transactions as they show in the online bank account transaction list OR do they have to be entered from the literal bank statement? (the online transactions are much easier to read)
Your goal is to put every transaction that has or will clear the bank into the bank account's register. It doesn't matter where you get the information to enter.
RE: 2. Am I supposed to create a company file for Personal so that I can enter the Personal transactions there (dinner, groceries, etc) OR do I just skip those entirely as far as entering it in QB?
Well, if you want to reconcile the account, then enter all the transactions that will clear the account. But, for the personal expenses, use an Owner's Equity account, as the owner is basically drawing from the business each time they do that. And, try to get them to stop doing this!
RE: 3. Actual Bank acct Transfers from Checking to Savings, Work Checking to Personal Checking (now that it exists), etc. There are several transfer transactions involving now 4 accounts (Wk ck, Wk sv, Per ck, Per sv) How do I enter these?
For the bank accounts you are tracking in QuickBooks, enter Transfer transactions between them. If you transfer into our out of a personal account not tracked in QB, again that is an Owner's Equity transactions (increasing or decreasing equity, for deposits and draws respectively.)
RE: 4. Is it correct to just enter Business1 transactions into that company file and Business2 transactions into that company file even though they are on the same bank account? (business2 is much "smaller" with very few entries)
If these are two tax entities, then putting them together can be a hassle at tax time, though some people try this and use Class tracking to split the P&L.
RE: 5. Credit Cards- the cards are all used for business. No idea what to do on this. The payments are paid from checking, of course. The balances are kept low to avoid interest or paid off.
It is again better to enter all the data for a credit card account in it's account register so you can reconcile it and so the payments make sense. Also better to not mix personal and business charges on the same CC account. But if that happens, then use an Owner's Equity account for the personal charges, just like the bank account transactions.
