Untangling Business Expenses Paid with Personal Funds

CCrum

Sorry for the long intro, but it may be needed to fully understand the depth of the intertwined accounts. I'm a sole proprietor in the US. I initially opened a Wave account in 8/20 to create invoices and help organize expenses for taxes for a job in which I'm considered an independent contractor (Company A). I also receive paychecks as a part-time employee of 2 other companies (Company B and Company C), whom I've been working with since late 2019; taxes, SS, medicare, etc are withdrawn from these paychecks already automatically. Taxes, SS, medicare are not withdrawn from paychecks from Company A. In Wave, Company A and Company B+C are listed as 2 separate income accounts.

I initially only had 1 personal checking, savings, and credit card account, as well as later adding in joint personal savings account to help account for routine transfers to/from those accounts and my personal checking account. Paychecks from Company A, B, and C were all deposited into my personal checking account initially. I opened a separate personal checking and savings account that are used as "Business checking" and "Business Tax Savings" accounts in 9/20. Since then paychecks from Company A are deposited into the "business checking" account and 1/3 of the check amount is transferred into the "business tax savings account" and taxes are paid later. Routine transfers (categorized as owner draws) are made from the "business checking" to my personal checking account as salary payment. Any paychecks from Company B or C is directly deposited into my personal checking account. The "business checking" account did not have a debit card associated with it until recently (11/21). I have the following linked asset accounts in Wave: personal checking, "business checking," and "business tax savings." Unlinked asset accounts include personal joint savings and personal savings. My personal credit card account is not linked and is listed as a liability account.

Prior to establishment of a debit card associated with the "business checking" account, any credit card purchases were made using my personal credit card. In the banking world, the personal credit card gets paid off monthly by the personal checking account (there's mostly personal charges + occasional business charges), and I was reimbursing any business expense incurred on my personal credit card account by transferring the cost of any business expenses from the "business checking" account to my personal checking account (not the CC account directly). To account for the business expense purchases and reimbursement in Wave, I created myself as vendor called "CCrum personal account payments", created bills for business expenses paid with personal CC (categorized in the appropriate expense category on the bill- ex uniforms), and recorded payment as bank payment from the "business checking" account. On the transactions page, it appears as a bill payment (description), owner investment/drawings (account), and withdrawal (transaction type).

1 ) was this the correct way (or a correct way) to account for both a) the expenses so they aren't counted more than once in the various expense account reports and b) the transfer of $ to reimburse personal CC expenses?

2 ) a) since I transferred $ from the "business checking" to my personal checking to reimburse myself (not to the CC account), do I need to have some sort of other transaction (maybe a journal entry) in Wave showing the credit card payment from the personal checking account and what would that look like? b) If so, would I just need to get rid of the bill payments and have 3 different journal entires- one for uniform expense purchase on CC, one for personal checking account paying off the CC, and one for "business checking" having an owner draw to reimburse the expense? c) If I do journal entires, how should I be categorizing the transactions from my linked bank accounts so they aren't listed as expenses multiple times?

3 ) it looks like now Wave has sections for both personal and business accounts in wave. a) should I take all personal and joint checking, savings, CC accounts listed as assets/liabilities and move them over to a personal account in Wave? b) if so, do I need to go back and untangle them all the way from the beginning, just starting in 1/21, or should I start w/ 2022?

4 ) Payments for other things like utilities, telephone, insurance, etc that are part business expenses, part personal expenses have historically been paid from my personal checking bill pay account. I have not been reimbursing myself from my "business checking" account in real life or in Wave, but they are categorized as expenses in Wave. a) should I be shifting $ over from my "business checking" account to reimburse myself for the business cost of those expenses? b) if so, what is the best way to do that?

5 ) I'm a sole proprietor- does it really even matter if business expenses are incurred on my personal CC to where I have to transfer "business" $ around to cover the costs?

Thanks for any help you can offer! Sorry for the long explanation leading up to the questions. I have a bad feeling I'm going to have to redo my entire account.....