Be Excellent To Each Other

Right, I'm having a bit of a Doc Gaywood moment and have suddenly decided that I'd like to desperately watch (legally obtained - Ed) videos. My only experience in this is a few years ago using Encode360 to convert some Lost mkv files to wmv format, which turned out very nicely.

I also have a few films in WMV format that also work ok, but here are my issues/questions:

I have an mkv file, which we just about managed to watch on the 360 last night using PS3 Media Server, although it was stupidly out of sync by the end of the file.
I tried converting the file to mp4 using XenonMKV only to discover that the 360 doesn't like mp4 files bigger than 4gig (I'm not talking about the Fat32 limitation here, I'm trying to watch the file from a HFS+ formatted USB drive).
Encode360 has been discontinued in favour of EncodeHD which seems to make mp4 files using the 360 preset.
I eventually got Encode360 up and running again on my laptop, but it didn't like converting this 7gig file.

Basically, what can I do to watch these files properly, or should I just stick to DVDs (Please note, I am willing to throw money at the situation if it will make things work - possibly in the form of a PS3?)

Yarr tip: Copy your ill gotten gains onto a USB stick to reduce noise from the drive.

As for formats, I use whatever my work colleagues bring in.

You'll be wanting the Mimi thread about the PS3 side.

Or you can just cut to the chase and download MKV2VOB. This makes nice compatible files.

Ooh, wait. I've only tried them through the media center extender bit. Might not work through the dash

Only a month ago as well, I'd forgotten about that one.
Ok, I'll make it short and sweet. Wireless seems to be very hit and miss (we only managed to watch this last night after I hooked my laptop up to the router), and I'm just a boring traditionalist that likes the idea of my files being on the device that I'm watching them on.
Does something exist that will allow me to watch a film that is bigger than 4 gig, from that device and without splitting the file.
I don't care if I have to convert the file, but preferably in a 1-button kind of way because I hate messing around with demuxing audio and video and then converting them separately and then putting them back together, etc, etc. Just assume I'm an idiot and give me something that has nothing more than a source file, a destination folder and a big fat GO button, thanks.