This is a hot topic. Maybe there`s no right or wrong? Maybe some applications are more suited to one medium than the other. Here are the facts and make of them what you will.
An analog recording is one where the original sound signal is modulated onto another physical medium or substrate such as the groove of a gramophone disc or the iron oxide surface of a magnetic tape. A physical quality in the medium (e.g., the intensity of the magnetic field or the path of a record groove) is directly related, or analogous, to the physical properties of the original sound (e.g., the amplitude, phase, etc.)
A digital recording is produced by converting the physical properties of the original sound into a sequence of numbers, which can then be stored and played back for reproduction. The accuracy of the conversion process depends on the sampling rate and depth. However, unlike analog recording which depends critically on the long-term durability of the fidelity of the waveforms recorded on the medium, the physical medium storing digital samples is essentially immaterial in playback of the encoded information so long as the original sequence of numbers can be recovered.
There`s a fundamental difference here obviously. When it comes to guitar it`s a worthwhile practice to consider your hands, guitar, strings, lead, and amp as the instrument – as a holistic whole, and it is this which gives the instrument its oneness, dynamism and character. Take a zen approach and aim for the guitar to be playing you rather than the other way around. The most natural-sounding overdrive devices are vacuum tubes – a natural-sounding overdrive will make use of playing dynamics and will respond to different string attacks with varying tones and levels of distortion. I like Mesa amplifiers and Soldano, but I rely upon some particular transistor amplifiers because built correctly they sound just as tasty. There`s a really good article here about speakers, transistors, valves, distortion and more.