I'm another 16-year Quicken hostage, with over 130,000 transactions dating back to 1992.
Downloading is overrated. It takes me less time to switch back & forth from my credit union's website to Quicken while reconciling my checkbook register than it does to fiddle with the download settings. Presumably Quicken et al can download checkbook data without errors these days, but that's certainly not the case for brokerage statements and for importing tax data into TurboTax. So don't expect that downloading will make your life easier or more enjoyable.
My advice would be to devote about $200 to trying every financial-management program you can get your hands on-- Quicken, Money, and shareware. Decide which user interface you like before you become assimilated. Because after that, resistance to upgrades is futile.