All digital owner here for the Wii U and 3DS. I think many people can be missing out by listening to what amounts to scare tactics and memes about Nintendo's digital infrastructure but rather than try to convince people of how good it is in comparison to other systems, I'll tell you why I have no problem going all digital at this point.
First of all, going all digital not only makes a ton of sense for a handheld due to the convenience Nintendo also has done the most to make me confident I will have my games on all future handhelds. Every digital game I have purchased across a DSi, a 3DS, and a 3DS XL are all on one system. Once I get a n3DSXL next year that will be four systems I have retained my games across.
I admittedly wasn't keen on purchasing digital games for the Wii but since they are still accessible on the Wii U it's nice but not great. There is less that convinces me that the games I have purchased for the Wii U will transfer cleanly to their next system and it may end up like the Wii again if the games are compatible at all but I have started this generation under the assumption that they have learned from not taking the Wii seriously as a digital platform. For one, they've made strides with the eShop even unifying the name and wallet (and account) across their handheld and console. There are day one digital offerings for retail games since launch and the ability to connect a hard drive. The quick start menu makes selecting a game a breeze. With my USB power cable for my hdd, all I need in addition to take my Wii U on the go are the Gamepad, the AC adapter, and the hdd with it's cable and possibly a USB charger cable for the Gamepad. It's still a ways from being comparable to a handheld but it's clear Nintendo is thinking in those terms based on the tons of speculation from fans and media as well as comments that suggest it is something they are keeping in mind. With a universal OS they will be able to make many of the possibilities a reality. Now, that may not mean that the features some people want like being able to share games across multiple systems or ease of downloading games on your account from whatever system you are playing on may be any closer, for me someone who has only one handheld and one console (that I'm playing at least) and rarely borrows games or resells them, I think whatever solutions Nintendo has in the future will still be to my benefit.
In terms of deals, I have saved over $140 on the WiiU since launch with the DPP. Additionally, the Best Buy sales on gift cards for the eShop have saved me/will save me over $150 on both Wii U and 3DS games. I have also bought many retail and indie games on discount if I haven't bought them day one. I've got deals on retail stores 3rd and 1st party games for up to 50% off and (some for free with promotions) and considering what the physical copies were going for at the time I think they were great deals even if I could have saved a little more on some since the convenience is worth it many times over. Having also gone all digital on my PS4 there hasn't been as big a discrepancy on deals as it seems people assume. In fact if I alligned launch dates I've probably saved more on the Wii U with my purchases due to the DPP and that I don't need to pay for PS+(which is debatable in how useful it's been to me personally).
If I had to do it all over, I absolutely would not do it differently. There are risks, some uncertainties, and decisions Nintendo has made thus far I don't agree with but going forward I am completely on board and I'm sure some people will look back and have more regrets that they didn't go digital than I will for going digital. I already had that moment with my CD collection refusing to trust or adapt. I wanted to be able to resell. I wanted the cover art. I wanted to share and find deals. None of that is worth it and I'm in the several month long process of ripping my music to a HDD now. Knowing there likely won't ever even be that option for console gamers going forward due to DRM (Nintendo or otherwise) makes me really pity you guys when you have the same realization about games and end up having to rebuy all the games you still want to play.