Hi @andrewhill…Welcome to Tiller!
I refresh my accounts each time I open the sheet. I am a little (a little?) focused on keeping my accounts up-to-date, so I try to do this every other day, at least. Many of the accounts are already refreshed since the last time I logged in, but a few lag and I simply refresh these manually.
I am in my third year using this product. At first, I had the same thought: If this refresh step were automatic across the board, it would be truly slick, but I have found that my watching the transactions pop in helps me confirm their categories, so I am more engaged with what’s happening.
I have found Tiller to be an exceptional tool for managing our financial picture. I have reviewed many of the others personally (Quicken, Personal Capital, Mint, YNAB)…none of them hold a candle to Tiller’s flexibility, reliability and ease of use. (And when you pair it with a mobile solution, like this or this, the value skyrockets!) The customer support is the best I have ever experienced. (That may sound like hyperbole, but its not: its true. These people truly care about and work to understand their customers.)
You won’t regret your choice! Hope this helps!
All the best.