I just paid for a year of Quicken Premier and have been trying to set it up. So far I have discovered that my 401k (guideline) cannot connect to Quicken, my Mortgage (Truist) can't import anything beyond the current balance, Robinhood doesn't connect at all, and Coinbase only seems to work with Bitcoin. Every single one of these works in Mint. I have other, more traditional accounts to connect to, but at this point I'm taking a break to decide if I even want to continue.
The most ridiculous part is that it seems to be borderline impossible to import excel/csv. So even if I wanted to suck it up and manually update half my portfolio, they've done everything in their power to make that as hard as possible. It appears that my options are to go hunt down some 3rd party application to convert csv to a format Quicken understands, or manually enter years worth of transactions. After exploring ImportQIF, it looks like its just a janky work around that breaks frequently with the subscription version.
Am I missing something here or is this paid software somehow significantly worse than free options? And if so, how do I take advantage of the "30 day risk free" period that was advertised to me?