Xero

Professional double entry software at a very affordable price
Accommodates both cash and accrual accounting
Links to financial institutions to get transactions
Uses standard importer recognized by the financial institutions instead of just trying to log in remotely (and triggering fraud alerts)
Can match multiple invoices to a single deposit transaction imported from bank
Can keep using Xero as company grows

Pre-existing expense categories/descriptions don't map 1:1 with IRS definitions, so I'm having to go back to all my receipts to make sure expenses are entered in proper accounts because I didn't realize this when I switched
More difficult to focus on specific expense categories to check transactions
Have not been able to import historic data from previous app (possibly because it's not double entry) so I am still paying the subscription on that software to retain access to my data
No integration with Craftybase, so I have to enter supply purchases and customer invoices there independently

Ease of use from a day-to-day perspective for a non accountant and integration with other cloud software such as Dext and Flowlens

We have had a couple of glitches where bank feeds have stopped working for periods of time, manual import of bank statements can take a few attempts to get right.

Provided it's set up properly, Xero is probably the most friendly accounting software - to non-accountants that is - of any I've ever come across. Back in the 90's, MYOB revolutionised accounting software for small business, but Xero takes it to a whole new level, by removing so much of the data entry work that takes time, leaves room for errors and is in general a pain, when you'd rather be - you know, running your business. With Xero, it's up to the individual operator how much they want to automate their accounting transactions; if you want to, you can use the really powerful, but still simple tools to do a lot of the legwork for you. If you prefer to do it more manually, that's OK too - it's still simple and very quick and easy to use.

Xero is constantly adding and refining its software. Inventory control is an area I'd like to see strengthened, but that's already way ahead of where it was a couple of years ago. Similarly processing payments in advance. But these are relatively small niggles which for the majority of small businesses don't present any issue.

What I like most about Xero is its open-platform ethos. It's not one particular feature, it's the whole way that Xero approaches what it does, and it shows up all over the product. One small example is how easy it is to manually import bank transactions via CSV file, and then how easy it is to undo that import if it went wrong. It's less about features (although Cash Coding and Find & Recode are brilliant) and more about design choices.

I want them to hurry up and integrate Hubdoc into Xero itself. And when that happens, I want there to be a way to generate a report that shows which GL transactions don't have a source document.