MD is not a cloud based product. Information is kept on your computer.
--- there are some internet based features, like downloading information from your bank, or syncing between computers/devices, but both are optional, and encrypted if you use them.
There is no subscription for MD itself. Ability to download transactions (via OFX) is never deprecated. There is a new subscription service called MD+, but it is optional. If you did end that subscription ($2/month), you would not be able to download transactions through that service, but could continue via OFX.
I don't know anything about Countabout, but there are ways to import QIF, OFX, to all accounts, and CSV to banking/credit cards (not investment accounts).