I think the main difference between using an external hardware unit and a software plugin is that you're likely to be recording the guitar 'wet' with a hardware unit (unless you record dry and then use an external fx loop from the DAW, which depends rather on the capabilities of your interface), but you have more ease of flexibility when using a plugin (typically the guitar is always recorded dry then and you can post-record tweak the sound to your heart's content).
At the end of the day, the guitar signal is going to be sampled, then maths will be applied to the samples, whether you're talking about a hardware unit or software plugin.
If you want to go analog, the SansAmp PSA-1 is very good but expensive. Too expensive for me when my original broke down, so I went for a Digitech DSP1101 which is somewhat more expensive than the Boss, but very nice indeed. I use a Rocktron Widowmaker for *clean* sounds; its a solid state analog, pre-amp only (no effects) unit but this would not be my choice for any overdriven or distorted type sounds.