I run a small online store and started with a single business checking account. Two years later I have PayPal, Stripe, a second checking account, a credit card for supplies, and a savings account I moved money into once and forgot about. Reconciling all of this every month takes me two full evenings and I still don't trust the numbers. I've tried spreadsheets and a free accounting app but I keep falling behind. At this point I'm seriously considering paying someone to clean it up, but I have no idea how much that should cost or whether it's worth it for a business my size.
Bookkeeping
I started with one account and now bookkeeping is a nightmare
Same thing happened to me. I opened a second account to keep taxes separate and it just made more to reconcile.
How many transactions a month are are we talking? That changes the answer a lot.
I'm a bookkeeper, so I'll say this plainly: a one-time cleanup is usually priced by the hour or by the number of accounts and months behind. You'll get wildly different quotes depending on who tou ask, so get two or three. More importantly, before you hire anyone, close or frezee every account you don't actually need. Every extra feed is a place for a mistake to hide.
Probably 200-300 transactions if I count the card and the processor payouts. The savings account has literally one transfer in it.
Then close the savings account. You said yourself you forgot about it.
The processor payouts are what always broke my spreadsheet. Stripe deposits a lump sum and the fees are baked in, so the totals never matched what I actually sold.
Same for me with PayPal bacck when I sold at markets. I ended up tracking sales in one place and fees separately, which sounds tidy but it just meant two things to reconcile.
One thing worth checking before you pay for a clesnup: whether the free app you tried actually imports the processor feeds. A lot of them do, but the setup is where people give up. If it does import them, you you may only need a few hours of someone cleaning up the mess once, not a monthly service. And no, I'm not going to tell you it's easy. It isn't.
is the credit card for supplies through the same bank as the checking account
Not sure that matters as long as the statements import. Mine are at different banks and it's fine.
I was thinking it might come in as one combined download. If it does, splitting the card out is its own chore.
It's the same bank. I hadn't thought about that. Honestly the part that Scares me is handing over all my logins to a stranger.
You don't hand over logins. Anyone decent will ask you to invite them as a user on each account or use read-only access. If they ask for your password, walk away.
I went through this two winters ago, and the cleanup cost more than I expected, but I'd do it again. The bigger thing was that it didn't stop stop at the cleanup. I still had to change how I did things or I'd have been right back in the same spot by spring.
What did you change, if you don't mind me asking?
Closed two accounts, got the fees importing properly, and set a recurring reminder to sit down with it for an hour on the first of the month instead of letting it pile up. Boring stuff, but it worked.