I have a Drobo FS. It’s a great backup solution, but not the most media-streamable NAS out there. I needed something that could stream video, starting out in various Apple-unfriendly formats up to 1080p, from my NAS to my iPhone.
First off, I tried the MediaTomb DLNA media server which installs directly on the Drobo — no attached computer required. Paired with the AirPlayer app as the DLNA player, that system worked well enough for sub-1080p video. 
AirPlayer handled all the various video formats very well (including non-Apple formats like AVI & WMV), but the hardware on the iPhone simply can’t handle downconverting 1080p. Enter transcoding.
Transcoding means your media server converts the resolution/bitrate to something else before firing it out to your playback device. So although the video may start off as a 1080p super-high bitrate clip, your media server downconverts it to 720p or whatever your playback device can deal with. The encoding can change too.
Here’s the current wolfpack of transcoding media streaming iOS apps:
VLC Streamer Free 
Good news: it worked.
Bad news: videos to be transcoded have to be selected individually beforehand on the computer, & they are dumped in your Application Data folder as a million small .ts files.
So, the only way to have a transcoded video library with VLC Streamer was to duplicate my entire video library. Deal killer.
Plex Media Server (yep, PMS)
Good news: The Plex interface looks really slick, both for the PMS web interface & their Plex player iPhone/iPad app ($4.99 but Plex is free otherwise). Plex does a really nice job displaying your media, pulling metadata & matching up cover art from various providers. Also Roku has a free Plex channel app, so you can stream video over WiFi to your TV. Neat!
Bad news: Plex doesn’t let you browse a nested folder structure. They used to, but not anymore. Instead they rely completely on metadata. Or you can restructure your folder structure to fit their models. Their “By Folder” view lumps everything together in one gigantifuck mess. My video library doesn’t have metadata & restructuring is not an option. ARRRHHG! So frustrating, so stupid. Pages & pages & pages & pages of Plex users agree.
Air Video
The good news: everything. So many good things, where to begin. First off, there’s no indexing. Install the Air Video media server & app ($2.99), pick a source folder or two, & you’re done. Thumbnails & transcoding are done on the fly & with no temporary storage on the server … unless you want that (nicely done!). You can stream media within your network or outside too, with or without server password protection. You can download converted clips to your iPhone/iPad for later playback, straight from the app.
Bad news: I honestly don’t have much to say. I wish there were permission levels for shares. Nothing else. Air Video wins.
Air PlayIt / Air PlayIt HD
Good news: Very similar to Air Video, & free! Has three preset permission options (admin, kids, public) that can be set on each share — this alone is brilliant. PMS/DLNA developers should take note. Why permission levels aren’t a standard feature on all streaming engines is a sad, thoughtless mystery. The wait once you click play on a video to transcode is nice & short. Air PlayIt also has the on-demand offline conversion option.
Bad news: Took forever to show the folders on the first view through the app – it waits to do indexing until the folder view is first requested, & then indexes EVERYTHING, while you wait… and wait… and … wait ….. it gets a little better on subsequent views, but all the waiting to just navigate folders is painful. I do have a lot of folders nested so maybe it’s a less common use case, but Air PlayIt server seems to be scanning the entire structure rather than just the section of the tree I’m viewing. Something’s very inefficient there.
Other than that, very good app overall, & can’t really complain that much for the price.
StreamToMe
At $2.99, StreamToMe is another very good option. I’m going to let TUAW.com take this one — if I wrote anything, I’d just be paraphrasing their StreamToMe versus Air Video review.
ZumoCast
ZumoCast was bought by Motorola & isn’t available for Apple devices anymore.
Any Others?
Any streaming apps I missed? Let me know in the comments.
Jesse
Thanks for the article. But mostly, this is just a shout-out for putting “windsurfing” in your header. It’s been a long-time desire of mine. If you know any good places to start learning in San Diego, let me know.
Wick
Oh man, don’t get me started. That’s great you noticed. Out here in Vermont right now it’s too cold to windsurf & the lake hasn’t frozen well enough yet for ice sailing… it’s that awkward in-between season doldrums. Arrrhggg! Must… wait…. and… be… patient… 🙂
Not many people learning to windsurf these days, so that’s awesome. It’s totally worth it if you can get past the early learning part where a lot of people bail. Once you figure out water starts & planing in the footstraps/harness lines, it’s fantastic.
I’ve never windsurfed out west, been up & down the east coast but haven’t made it over your way yet. But I dug around a bit & Mission Bay Aquatic Center looks really good, fantastic rating & comments on Yelp. $150 for four 3-hour lessons, or $220 for that plus 6 more hours. Looks like all the gear is included so that’s a good deal especially if you can get into a small class.
Good luck, hope you go for it.
Mik
Hmmm… But weren’t you trying to pull media straight from a Drobo?
All of the solutions you mentioned require your Mac to be on, too! pulling the media from the Drobo, doing the transcoding then streaming it you your iPhone/iPad/whatever.
Any idea about what iOS applications can successfully pull media as-it-is from a network share (Drobo/Synology/WD MyBook Live…) and then play them?
Wick
True. The problem is that for 1080p video, my iPhone 4S needs transcoding & the only way that happens is with the help of the workstation. Maybe MediaTomb will add transcoding someday, but even then I doubt the current Drobo models could handle processing 1080p video on-the-fly.
The Air Player app (not to be confused with Air Video or Air Playit) did a nice job of playing the native formats, but it’s limited by the processing power of your device — that might be your best bet.
I think the only other solution would be an app that grabbed the full media file, transcoded it using your mobile device, then played the converted file. But I don’t think an app like that exists…