Not a popular opinion around here with all the BIG G fan-boys, but I'm with you: Garmin's update system/software/user interface absolutely SUCKS! I have NO issues with ForeFlight updates, but it seems I'm always dealing with some new problem with Garmin. In this day and age of IT, these issues are inexcusable IMHO. The Garmin Database Manager is pathetic in today's standard of usability.
I have to deal with the proprietary data cards for my GNS430W which require a special card reader, but it sounds like your GTN uses SD cards? If so, I can vouch that a cheap adapter for your iPad is the way to go; I use that to upload my data from my Insight G3 to Savvy with no problems. Granted, I can't speak to how well the Garmin Database Manager is going to react! But, since the FS510 thing isn't working out for you...you're going to need something to update your GTN! As far as EFB, no way I'd be paying for BOTH Garmin Pilot AND ForeFlight.
Good luck!