How important is reconciling accounts for a small LLC (Quickbooks)?
I would suggest opening a new account (credit card and bank) for just your business. This protects you in multiple ways, but is no bigger burden for you other than carrying another card in your wallet.  Then QB can download the transactions from your website and reconciling is a cinch. If you got audited, you'd be in for a world of pain right now.  From personal experience there are a few charges that go unnoticed that reconciling finds every month at our business.  We have a very strict process in place, but some things slip through the cracks.
After talking to two CPAs it seems like managing it using an imprest system is the best idea. The base characteristic of an imprest system is that a fixed amount is reserved and later replenished as it runs low.  This replenishment will come from another account source, e.g., petty cash will be replenished by cashing a cheque drawn on a bank account. Petty cash imprest system allows only the replenishment of the spend made. So, if you start the month with €100 in your petty cash float and spend €90 of that cash in the month, an amount of €90 will be then placed in your petty cash float to bring the balance of your petty cash float back to €100. The replenishment is credited to the primary cash account, usually a bank account (Dr - Petty Cash a/c, Cr - Bank a/c) and the debits will go to the respective expense accounts, based on the petty cash receipt dockets (Dr- Expense a/c, Cr - Petty Cash a/c). In a non imprest system where a fixed amount is issued every month, e.g., €100 every time cash is required, there is no incentive to ensure all money issued has been documented because when money is all spent a check for a fixed amount is issued. It is much more difficult to reconcile a non imprest system as you never know how much exactly should be in the float. In an imprest system the amount requested is documented, the documentation being the petty cash dockets and their associated receipts or invoices. So at all times you can check how much should be left in the petty cash float by deducting the amount spent from the opening petty cash float. You can make a capital contribution, not a loan. It's not a taxable event, no interest, and you can take a distribution later when the business has the money to pay you back. So yes, transfer the money. If you use software like Quickbooks, make use of unique accounts for tracking the contribution "For anyone that's curious, I had a number of chats with Quickbooks who recommended I import only the relevant business transactions from my personal account & personal credit card in order to lower the tax liability. This way money ""paid"" from the business account to myself rightly shows up as a transfer and not as income. This means when generating a tax report, it calculates the correct rate of tax to be paid based on income minus allowable expenses, regardless which account they came from." "Money management is data-driven.  You've been operating on ""how you feel"" and ""what should be"", and that's why it hasn't been working.  First you collect data on how you actually are spending money.  Record every expenditure and categorize what it was used for.  Go back 6-12 months if you can.   You don't need blistering detail, in fact I adjusted my lifestyle to make that easy.  Fast food meals, movie tickets, USB cables, anything too small to bother recording, I just pay cash for that. Everything else:  check, ACH or credit card. It is not excessive to do it in Quickbooks or similar if you know the app.  Whatever is most efficient for you.  Now you have a log of what you've been spending on what in a time oeriod, and a log of your income. Congratulations, you have a ""Profit & Loss Statement"", a basic financial planning tool.   Now you can look at it accurately, decide if the money you are spending in each department brings the value and joy that fits the expenditure,  and change what you want. You may decide you'd rather save $1000/mo than run a $200/mo deficit.  Changing is simply coming up with different numbers that you think are achievable.  Congratulations, you have a budget or spending plan.   Again, data driven.  The point is, your spending plan is based on your actual experience with past expenditures, not blind-guessing. Then, go out and make it happen." Your account entries are generally correct, but do note that the last transaction is a mixture of the balance sheet and income statement.  If Quickbooks doesn't do this automatically then the expense must be manually removed from the balance sheet. The expense should be recognized on the balance sheet and income statement when it accrues, and it accrues when the prepaid rent is extinguished when consumed by the landlord, so that is when the second entry in your question should be booked. The cash flow statement will reflect all of these cash transactions immediately. I like Quicken for personal use, and they have a small business edition if you don't want to move into QuickBooks. So long as you don't hate what you are doing, I'd say the price is somewhere in the neighborhood of $100-200 year of income to be worth the bookkeeping. I'd only say more than that if you have a ridiculously complex tax situation, you have an irrational hatred of filling out a few forms once a year, or if you just have such a stupidly large amount of money that even having a few hundred dollars a year to donate to people in desperate need just doesn't mean anything to you. Or if you are under special income limits and just a few dollars of income would put you in a bad situation (like a loss of medical benefits, etc). The reason is actually quite simple: the taxes aren't really that hard or time consuming. I've handled three self-employment businesses in my life, and unless you are trying to itemize every last dollar of business deductions and expenses, or you really want to scrape out every last cent from minor deductions that require considerable extra paperwork, it's a few extra forms on your taxes. Most of the extra taxes are as a percentage, so it reduces the benefits, but really not by much. You don't have to make it extra complicated if the extra complexity doesn't give you a big payoff in benefit. I would suggest you pick the simplest imaginable possible system for accounting for this, so that you might only spend an extra few hours per year on the books and taxes. Don't keep $10 sheet music receipts if you feel it's a burden to try to itemize expenses, etc. Instead, the decision should be if you (or in this case your wife) would enjoy doing it, and bringing in money can just be nice in it's own way. I'd suggest she keep some out for little extra niceties, earmark some for feel-good charitable giving, and then of course sock away the rest. Don't let extra income be an unnecessary burden that prevents you from getting it in the first place. What I would prefer is top open a new category charges under dispute and park the amount there. It can be made as an account as well in place of a income or expenses category. This way your account will reconcile and also you will be able to track the disputes.