Frequent users of arrows and other characters that are hard to input via the keyboard should better set up such shortcuts as text replacements, be it via the System Preferences in OS X (Keyboard → Text) or third-party tools like Typinator, TextExpander etc. I’m sure there are similar tools for other platforms, too. This not only avoids messing with the semantics of the underlying text layer. It also works system-wide and independent of OpenType support, and one doesn’t have to memorize which font used —> and which one –›.
This question intrigued me and I ended up doing a quick internet search on it for Korean typefaces, which represent a kind of a parallel history to the development of type in Europe.
In Korea the typefaces produced by the national type casting foundry during the Joseon period were referred to by the names of the year that they were produced in the sexagenary cycle. So the first one in 1403 was named Gyemija (also romanized as Kyemija; 계미자 in hangul, 癸未字 in Chinese characters) because 1403 was the gyemi (癸未; guiwei in Chinese) year. The most famous Joseon-era typeface, recast several times over the next couple of centuries, was first made in 1434, the gabin (甲寅; jiayin in Chinese) and thus was named Gabinja (also Kabinja; 갑인자, 甲寅字). The scholar Kim Jongjik (김종직 in hangul, 金宗直 in Chinese characters) explains these names in a piece written during the reign of King Seongjong (r. 1469–1495).
These are generic names, obviously, but Gabinja was also sometimes called Wibuinja (위부인자 in hangul, 衛夫人字 in Chinese characters) after Lady Wei (衛夫人), a famous Chinese calligrapher, supposedly because of similarities of the typeface to her style. Somewhat similarly, Iminja (임인자, 壬寅字) which was produced in 1782 is also called Hanguja (한구자, 韓構字) because it was based on the handwriting of Han Gu (or Han Ku; 한구, 韓構).
So what was the first Korean typeface that was given its own name not based on the year it was produced or the hand that it imitated? According to this book, the first non-generic name for an officially produced typeface was Saengsaengja (생생자, 生生字), a wood type from 1792 (which was named by King Jeongjo himself according to the book). It is named after a passage from the old Chinese classic, I Ching (易經), also known as the Book of Changes: 生生之謂易 (shengsheng zhiwei yi), or "production and reproduction is what is called (the process of) change" (Eileen Chang's translation). 生生, "production and reproduction", is simply the doubling of the Chinese character for "life" and is also translated as "life and growth" by other authors. I find it a quite fitting poetic name for a typeface.
Nothing is more humbling than looking at something you were proud of last week. Be heartened though, this is the Type God's way of letting you know that you are beginning to be able to see. The cure is to keep drawing. Keep looking. Keep fixing. Mostly, not to look on it as a failure in drawing, look at it as a victory in learning to see. If you want to design type, get used to that feeling, and even take pride in redoing, it means you are growing.
Sometimes it really pays to be conventional. I've tried being more permissive with my agreements over the years and I've found that it was often confusing to customers. I included acquiescent features such as allowing unrestricted application embedding or roll-your-own web embedding; allowing open-ended in-house font mods and other EULA curiosities. I tried making the wording clearer and even included diagrams. I think the problem wasn't my lack of clear explanation, the problem was that I was offering something too weird. Agencies would often ask permission for features that were already stated painstakingly plainly in the agreement. Sometimes they'd make me print/sign/scan (sometimes mail) release forms and custom agreements. I had quite a few customers tell me that they'd prefer a more conventional agreement because that's what they're geared to deal with. After three years of that nonsense, I switched to a bog-standard agreement and all is well.
The rotunda broken r presents an interesting design problem for roman types used to transcribe manuscripts. A peculiar convention of some transcriptions is to set an e.g. bastarda, rotunda, or other blackletter manuscript in roman type, while at the same time representing some of the graphotactic elements of the original text, such as the use of the broken r. Hence the inclusion of the ꝛ as a distinct character in Unicode, allowing plain text encoding of such transcriptions.
I've had two occasions to design broken r forms for such use. The first was an extension to Times Roman being used by a scholar working on a mediaeval Bible commentary, who was very particular about the 2-like shape and wanted a form that would ligate with a preceding round letter:
The other was the Brill types, for which I also had to imagine how the form should be constructed in an English roundhand inspired italic:
I was, then, pleasantly surprised to spot an example written by Joseph Champion for George Bickham in 1741, using the same construction as I had imagined: