A little late here as well.
IMO , you really want to have H265/HEVC playback (not just for 4K - encoding to it can half the file size of most HD videos without perceivable quality loss in my experience). It's fast becoming the standard for HD video distribution. The drawback is it requires an exponentially larger amount of CPU power to decode compared to previous codecs.
It's also important to be able to access USB drives over 2 TB; The 128 bit indexing perplexes many older linux and android usb stacks - that means many of the external drives are useless on them - Swapping multiple 2TB USB 2 drives is a pain and more expensive than a single larger drive.
If using USB exclusively, Windows (Samba) Share playback isn't necessary, but having just purchased a Roku 3 which won't (not can't - they just didn't program the functionality) do that, having it lacking is horrible IMO.
I've never used MakeMKV - I encode DVD to H264 or H265 in Vidcoder (Handbrake interface) with 3:2 pulldown detelecine. The drawback to that is the individual tweaking necessary for consistent quality. It can get complicated to tweak the aspect ratio, deinterlacing, cropping, audio downmix etc. I also often have to trim large files down to individual episodes or make multiple attempts at an encoding to get the post-processing right. Also, at the quality I use it can take a while, even with a recent i7 processor to encode a final archival-quality video file.
MakeMKV is flawless in it's simplicity - I think you made the right choice considering the number of discs you're processing.
Because you're ripping full lossless DVD quality to MKV, you'll need to ensure that the media player handles the deinterlacing properly when playing it back. The result might be different on a 480i CRT or a HD flatscreen depending on the player. That functionality is kinda a tossup - it's a flag in the open-source Mplayer core most of these media boxes use, and an unknown until it's tested.
The only for-sure I know of with DVD playback is the WDTV media players - they flawlessly play back .ISO DVD rips with full interactive functionality in my experience. I played through the DVD edition of Dragon's Lair on a 2nd Gen WDTV off a thumbdrive. Still unknown if that functionality would hold for a transcoded MKV, tho I'm happy to test this.
If you haven't purchased a media player box yet, I can test a tough-to-deinterlace DVD-to-MKV video on a handful of devices for ya.
Currently around my house plugged into TVs or (mostly) collecting dust:
WDTV HD 2nd Gen. (WDBABF0000NBK-00)
WDTV Live Plus (WDBABX0000NBK-00)
WDTV 2014 "Non Netflix crap edition" (WDBYMN0000NBK-00)
MP018 1080p Media Player (DX:55119)
Netgear NeoTV Max (NTV300SL)
CX-919 Quad Core Android HDMI Dongle (DX:217792)
Sony Blu-Ray w/ Wifi (BDP-S3200)
Roku 3 (4230x1)
Nvidia Shield TV (P2571)
I no longer have any Star Trek-TNG or Voyager DVDs, tho they're the most notorious for being horrible to deinterlace (the starfield in the windows was interlaced at a different synchronization to the live-action). Even Netflix version of Voyager is still a mess.
Except for the last 2 (or 3?) on that list, they're all mostly useless to me and they're piling up. I'd trade most for a handheld cart or $10 and the cost of shipping. Some I've never used, but mostly they're listed in the order of their capabilities.
The 2nd Gen. WDTV overheats if played for over 6 hours (without fail - I've bought tons of these). Some Highcode H264 make it overheat and fail.
The Live Plus is still my favorite - it can't play H265/HEVC so it became obsolete instantly. It needs a dongle to use Wifi.
The WDTV 2014 is a trainwreck. It's USB playback support seems solid. No H265
Mp018 - Never even unboxed - no H265. 5/5 reviews - it is the cheapest one I ever bought.
Netgear - Friend gave it - says it crashed. Might try plugging it in.
CX-919 - Really cool. Wifi and Bluetooth range suck really bad. Best smart TV conversion ever if it could do internet over 10 feet from the router.
Blu-ray - Wins the functionality over previous - interface is all text - Plex support is crazy nested text trees. No Samba share playback. Great device except family abandoned Blu-rays and gave them all away 'cause Netflix.
Roku3 - Commercials and shoehorned functionality. Not used to these limits - it's powerful and cheap. Plex support is fully working - that's all that matters.
Nvidia Shield TV - Most expensive for a reason - it is the most powerful and functional Android device I ever owned.
I guess the first priority is to figure out which can play your MKVs. I'll use MakeMKV on the Gorillaz - Slowboat to Hades disc and see which device fares best with it's obscure "tour" interface for video payback - once I sleep off some beers.