It's not trivial ,, it's a friggin mine field.
Many roads lead to Rome.
Start by asking What style of music you wish to play.
Rock, Country, Jazz, Folk, Trash metal, get the picture? Every style requires a different approach.
I have a mate who owns 30 guitars, at least a dozen amplifiers and has just purchased an all digital pedal and I'll bet that buzz will wear off in a few weeks and he will go back to playing his Old classic 6V6 Fender deluxe.
All I own is a couple of Amps and 3 El guitars and 2 Acoustics. My pedal board gives me all that I need.
Sure my needs are simple as I sing and play but I'm often asked to play lead backing for some folks. I have 4 main sounds that I use so I don't need 127 patches to produce a decent sound.
But if you are chasing all the slick sounds (and you actually have the talent

) they have a lot to offer then just visit a lot of music shops and try them out.
Keep in mind no matter how much money you spend on digital gear with all the clever IR stuff,, I've noticed a lot of players end up returning to the older analog FX.
As for your Q about Fender Emulator into a Vox,, Obviously it will change the outcome,, whether that will be rewarding will depend on whether or not you have ever played a real VOX or A Real Fender,, and which models and which guitars were used as reference, were you in a big hall or in your bedroom with a carpeted floor. And,,And ,,And
My way my rig setup FWIW,
All my pedals are buffered except for one.
I Don't try to get all the drive in one pedal,
I use 3 dirt pedals and gain knobs are always low. This allows each one to build more drive and edge into> A slick chorus pedal, > Didgi Delay, > Optical Compressor,> Cab Sim, > PhAbbtone,> into a very basic old Laney SS Amp consisting of (Treble Bass Volume) which has a spring Reverb for a bit of ambience.
Optical Compressor is thanks to Member Mictester and his "Really Cheap Compressor" circuit build on this site.
The PhabbTone is my own design as are 2 of my dirt pedals.
Although I own a lovely real Strat my favorite is a cheap copy with Ceramic PU's which has a sweeter sound than my 2 other guitars.
Re Cab sim,, sounds hi teck,, but really it's just another way to alter the tone shape of the signal. I use an Analog unit loosely based on the Rockman circuitry. Of course IR stuff gives a pile of extreme options at the press of a button.
Regards Using FX loops,, I've never understood the benefit.
It does make some sense with SS rigs but with A Good Valve amp you can easy loose the magic when the HT voltage starts to sag the whole amp. Inserting out board circuits breaks the preamp from the main power stage.
But for modern Metal amps it's all preamp distortion so you would hardly notice.
Now that's an old fart ranting

,, Better minds here with far more experience will have far more options for you to seek out.
Regards, Phil.