Moneywise is I believe is financial software for Android Phones. These forums are for Moneydance Personal Financial Software for Windows, Mac & Linux with helper applications for Android and IOS, so I question which software you are looking at.
Welcome to the MoneyDANCE forum. Assuming you mean Moneydance - which I believe you should consider, as I have done so as well, here are answers to your questions as if you meant MoneyDance.
Conversion works well - I have 20+ years of data - as regards credit cards, cash accounts, bank accounts, and securities/stocks/bonds. Not so much for cash balances in investment accounts - but you can USUALLY adjust that by putting in an offsetting initial balance in MoneyDance as long as you don't care that your historical cash balances in your investment account are wonky. (The last item is not a deal breaker. Just I am working on it for myself.)
You can definitely download a fully working version of Moneydance for free. Only limitation is 100 manual entries maximum. After that you must buy it, but still have 90 days to ask for a refund.
You ask how often SHOULD Moneydance be upgraded - should is different for different people. Charges are incurred for year upgrades - Moneydance seems to upgrade every couple years.
Moneydance doesn't expire online access like Quicken does (yay!).
They do ONLY support direct connect, for security reasons, so SOME of your accounts may not download, though they do have alternative ways to get the data, just not automatic.
I'd recommend giving Moneydance a try, even if you really did mean MoneyWise.