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There is so much crap out there that I just don't think it is worth buying unless you are actually paying for a premium quality product or package of products.
I say go for the freebies, but do a search of them, as you can end up with a lot of junk VSTs that you will never touch and it just ends up slowing you down.
In terms of instruments and effects actually worth paying for, in my mind would be all the quality stuff, that simply do not hold any comparison to free stuff: Native Instruments Komplete (pricey yes, but very worth it. It would be the first thing I recommend), VSL (if you are into orchestral stuff.. more of a niche thing), Omnisphere, Waves stuff, PSP Vintagewarmer, Maschine (not strictly software), fabfilter stuff, and maybe a couple other standard type of instruments like Sylenth or Z3ta.
I have quite a few softsynth purchases that I regret wasting money on, as they've never really been touched, and they just sit there on my computer. Really, every synth out there seems to promise to be truly groundbreaking and analog, but most of them are just pieces of shit compiled on SynthEdit by a 1st year ComSci student with no thought to ease of use or musical usefulness.
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