@Brett Sayers Based on your posts, I can see your frustrations. I find that Intuit has better support with QBO than QB desktop, I think since that's the future and probably they will eventually phase out the desktop version, who knows. There are also features for QBO that are not available on desktop so you might be paying more but will spend less time.
Let me see if I can answer your questions
1. The proper way to enter the security deposit is. a. Create an invoice (using items Security Deposit mapped to Security Deposit (liability account). b. Process received payment, Deposited to Checking account. As an alternative, you can skip step a & b and process a Sales Receipt instead. c. Process a "Transfer" from checking to the savings account. The reason why I like processing it as an invoice is that when you go to customer account, it will show up under Transactions. But if you insist to enter it using Register entry method, sure. a. The deposit in the checking account should be categorized as Security Deposit, then the "payment" (which is actually a transfer to savings) in the checking should be booked using Savings account as category.
2. When you set up a bank, credit card or loan account, you will need to determine what is the starting date you would like to track for all accounts. So say you want to start 10/1/20, then get the balance as of 09/30/20 for all your accounts and set that up using the Opening Balance category. It appears like you are doing the reconciliation incorrectly since the journal entry created by the system usually pops up when you are forcing the account to balance. Also, once the account is reconciled, you are not supposed to be deleting or changing the amounts, otherwise, it will throw off your beginning balance of the next reconciliation and messes things up. Reconciliation is a must, you just need to do it right.
Honestly, if you hired a professional, the set up should have been done in a few hours and a 2-hour coaching session should have covered pretty much what you need to know (at least the basic) to get you going with the day to day bookkeeping of your business. The hourly rate may be expensive but the amount of time it will take them to do it will be way less than the time you spent trying to figure it out. I'm not pitching anything, it's just a reality. The good thing is since you spent many hours learning it, when you do finally to ask for guidance, it will be easier for you to pick up what is being taught.
Quickbooks is a generic software, but if it's set up right along with your accounting process, then you will appreciate more. Good luck!
