I don't understand the justification of spending $1,000 on a font like Helvetica Neue. Is this something your business purchases for you and even then, why is it better than the myriad of free fonts you can find?
It mostly comes down to two things: attention to detail, and scale.
For example, a good, professional quality font that is designed for screen use will contain “hinting” information so that it fits well to the pixel grid at smaller sizes, including at typical body text sizes for on-screen reading. If you drew your perfect font in a vector format but then just scaled it directly without regard to the limited number of pixels available, you’d see all sorts of ugly artifacts.
A good font designed for printing, on the other hand, will probably be full of small adjustments like ink traps where lines cross and having curves actually go slightly outside the design rectangle for a particular glyph, because these minor distortions make the font appear cleaner and more consistent in design to the human eye, even though under a magnifying glass you’d see that the opposite is actually the case.
If you asked a lot of designers for an acid test, they’d probably tell you to look at the kerning, i.e., the spacing between glyph pairs. In a good, professional grade font, the spacing will be even, and so will the colour of a text block set in that font. Awkward spacing is the hallmark of amateur work, and is unfortunately so common that serious DTP software like Adobe’s InDesign now includes an “optical” kerning option that overrides the settings built into the font and makes its own guess at how to even things up based on the shape of the glyphs.
As far as scale goes, consider that a typical free font contains enough glyphs to support a few Western languages: the Roman alphabet, digits 0–9, common punctuation, and perhaps a few accented characters. A professional font designed for international use might offer 1,000+ glyphs, covering a much wider range of alphabets, ligatures, specialised punctuation marks, different kinds of digits (believe it or not, there are at least eight common variations of the digits 0–9), multiple variations of the same letter or digit, and if you start getting into the wizardry of modern OpenType fonts in styles like calligraphic scripts, the sky is the limit.
As a final example, again a matter of scale, a typical amateur font family might include regular, bold, italic and perhaps bold italic fonts. A professional font family probably offers a wider range of weights, sometimes as many as nine or ten. You’ll usually get a true-drawn italic if there is an italic at all, where amateur fonts often just slant the regular version, particularly for sans serif designs. You’ll probably also get true-drawn small capitals if you’re talking about a font intended for setting body text. You might even get a whole set of subtly different designs, sometimes called optical variations, intended for use at different sizes. As with many of the other details, the idea is to exaggerate or tone down certain aspects of the design so that for example a caption version doesn’t look too fussy, while a large version to set a book title doesn’t seem too clunky.
Ultimately, this kind of scope and level of detail takes a huge amount of time to get right, not to mention having the skill and good judgement to do it at all. Since there’s a relatively limited market for really good work in typography — plenty of people will settle for “good enough” — those who offer it charge accordingly.
And so, to my answer to the original question. If I had to pick five “go to” fonts today, and assuming we are really talking about font families here, these would be the ones for me:
- Arno Pro Opticals: my favourite serif design at the moment
- Myriad Pro: a flexible, general purpose humanist sans
- Avenir Next: a reliable geometric sans, clean but somehow not as chunky as say Futura
- Verdana: tried and tested screen-optimised font for web sites, which is installed and renders well on just about anything (except the occasional mobile device, but they all have good alternatives you can fall back on)
- Consolas: anyone in software needs a good monospace font, and this one works well both on screen and, if you need it to, in print
Not coincidentally, my first three choices there all come with a comprehensive range of weights and styles, including gorgeous italics and swash variations for the serif, and condensed variations for both Myriad and Avenir. It’s a shame that Adobe seem to have an aversion to designing useful small caps (Arno’s are really petite caps, and Myriad doesn’t have any at all) but apart from that there’s very little missing for typesetting non-specialist jobs anywhere in the Western world.