I've been a Line 6 man (until I got a VOX Tonelab LE) but I haven't used either the pocket POD or the Toneport. However...
I understand the pocket POD is based on the older POD 2.0 modelling and as well as that has very little in the way of programmability - if you like the tones you're away, if not, not much tweaking available. Not sure what its outputs are. But as far as I'm aware, it is designed as a "cut down pod for travelling with".
The Toneports are actually designed for PC recording. I believe they use the (better, in my opinion) POD XT modelling. I think they work as a one-stop modeller and sound card - I think they even have mic inputs. I did consider going the Toneport route when I bought a POD XTLive, but I already had the soundcard capability, my PC isn't really up to supporting the modelling as well as my DAW, and I didn't want to switch on the PC everytime I wanted to play... so I plumped for the standalone unit.
Of the two, I'd go for Toneport. But if you like the pocket POD sounds, consider a POD 2.0 - I used one for recording for some time a few years back. There still seems to be lots about, and they seem to be going new for quite cheap. It's robust, very versatile, and if you have a midi interface to your PC you can download a free patch editor/library program that makes setting up tones a breeze... (it has line outs, but no sound card built in though, )
But do consider this: "The old lady passed 100 bucks my way to do as I please" - are you sure that doesn't mean take her out for a nice meal?!! :lol: