I’m not 100% sure what the differences are and would like some input, thanks.
Also, I was wondering what the second pickup position did (bridge + middle).
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SSS is the original pup configuration, as Leo saw it around 60 odd years ago. At the time, the pup selector switch was simply 3-way. Bridge/middle/neck. We found out that by careful positioning of the switch, it could work as a 5-way, introducing bridge + middle and neck + middle combinations. After a while, Fender changed to a proper 5-way switch, as we see today on all Strats and Stratalikes. Also available, out of interest, was the Supreme, with 3 push buttons, offering the rare neck+ bridge combination not available with a 5-way switch. Even 'all off'!
Much later, the humbucker (H) was invented, which is effectively two pups in one. It cancelled out the noise some single coil (S) pups produced, and also, gave a fatter sound.
On some guitars, two, sometimes three humbuckers were installed as standard, and others had a mix. As in HSS. There's more variety in sound produced from HSS, although some prefer the original SSS sound, which is one reason they're still produced prolifically.
HSS is usually a bit more expensive, but at the end of the day, the choice is down to the individual, and his preference in sound (and size of wallet). I think there may also be options with push/pull pots, which put pups in or out of phase - giving yet another option for tone.
I actually have an HSS Squier. I have not played an SSS however I can say the following.
Firstly, for clarity, a traditional strat has an SSS configuration.
Getting the humbucker (HSS) version makes the guitar more versatile as it is your first guitar, although personally I have found that the bridge position is not the most useful position for a humbucker. Humbuckers are traditionally described as having a "warm" sound however I have found that in the bridge position it is very bright, sometimes almost unbearably so, although that could be my amp. So don't be mislead. Despite this, the humbucker can provide some rich distorted lead tones if that's the style of music you want to play.
However, the bridge single coil on a traditional strat is often regarded as the least useful/versatile pickup, as it has an extremely bright "twangy" sound. Most of the time people will play using the neck or middle pickup. In this way, the humbucker makes the bridge position more useful than it would otherwise be. The one style of playing where the bridge pickup is often used is funk, although personally I don't miss it on my HSS strat and the middle pickup still gives a good funk tone (and personally I have found that using the middle and bridge pickups on the HSS strat at the same time gives a nice thick funk tone).
So if I had the chance to purchase again I would still choose the HSS. Despite the fact that the humbucker isn't the most useful in the bridge position, it's more useful than a single coil would be and to tell the truth I use that pickup a lot for solos. You just need to be careful to dial the treble back a bit on the amp otherwise it can come across too bright especially if distorted. But personal preference will probably factor a lot so your best option might be to try out both versions in a store if you can.
It should also be noted that if you want to change/upgrade pickups later on, you will be restricted to always have the humbucker in the bridge position because the cutouts in the body and pick guard are the wrong shape for a single coil.
Also to answer your other question about the pickup selector switch, it works as follows. The pickup selector has five positions. The first position is the neck pickup, the third position is the middle pickup, and the fifth position is the bridge pickup. The second position combines the signal from the neck and middle pickup. The fourth position combines the signal from the middle and bridge pickup. Also, the first tone control is for the neck pickup and the second tone control is for the middle pickup (there is no tone control for the bridge pickup). Of course, if you're comfortable with modding it, you can change this however you want but this is the standard configuration on (I believe) all strats.
It depends on what kind of music you want to play.
An HSS strat has a humbucker in the bridge position, an SSS strat has a single-coil pickup. As the name implies, the humbucker by design suppresses hum (annoying noise picked up through electromagnetic induction from the mains electricity, amps etc.). It usually has a higher output level (adding the output of two sets of coils). It also filters out some high frequencies. Humbuckers are thus better suited for high-gain (strongly distorted) amp settings - less noise that gets amplified along the way, earlier saturation - and therefore the standard choice for hard rock and metal.
If you don't care about that (say, all you want to play is funk or pop), you can go with all single-coils, which produce the typical strat sounds (stereotypically: thinner, brighter, snappier, twangier than humbucker sounds).
The second pickup position combines the signals from the bridge and middle pickups. Similar to a humbucker, this leads to an amplification the base frequency (the amplitudes are added), but a suppression of some overtones (but at different wavelengths than with a humbucker). That apparently results to a sound with a unique quality. AFAIK, it doesn't suppress hum, though.
You can find videos on Youtube that demonstrate each position, or you can go to a guitar store and try it for yourself.