As mentioned your welcome to ask Garmin to transfer maps and updates to the 496, but it’s highly unlikely that they will agree. Maps and updates are tied to device and non-transferable. That has been the case for the last 14 years or so. I’ve had the same problems with connecting to a Mac, and I haven’t got it sorted. The GPS pops up a message saying the USB is connected, but the Mac doesn’t see it. I’m using a old XP laptop, but I’d much rather use my Mac. I’m not sure the issue is hardware or software, so if you can boot your Mac to Win7 using Boot Camp, I’d try it. I tried windows inside a VMware vm and it didn’t work, but that doesn’t have direct control of the hardware so a dual boot may have better luck. I’ve never used express or lifetime updates, but I’m guessing that that will be a requirement if you want to buy lifetime updates for the 496. As for whether you are better with the Zumo or 496? The 276-496 series were, for years, the most desirable Garmins for lots of reasons. They are great GPSs with some awesome capabilities. For that reason Garmin kept selling them even after they obsolete in terms of hardware and compatibility. Realistically making them fully work with modern PCs and Macs is less than ideal. The memory card is strange and archaic with limited storage capacity. Even if you get a reader for the Garmin Data Card, it doesn’t behave like an SD card where you can just copy files. You have to use Garmin applications to load data to the cards. All of these things mean that if you want the level of PC integration with the 496 that you get with new GPSs you need to be prepared to jump through some hoops to make it work. If you do that, you get one of the best GPSs made. On the other hand if you don’t want to deal with old tech and you want something that requires a lot less manual futzing and is more or less turn key, then a more current model may be a better idea.