I don’t really keep track of how long particular glyphs take to design and draw, but I do recall that each of these took what seemed like a whole day. The manicule was the result of a lot of research and drawing; while I had great difficulty resolving the components of the superellipse ampersand, which I had also tried in different shapes (e.g. closed loop at the top, and no diagonal), there being three or four developed alternates that were discarded.
Press gain is not so much of an issue with oldstyle or transitional faces. The problem for newspapers was the predominance of didones, and crude printing, but that is history now.
My strategy for the Pratt fonts, for a paper which has both coated and uncoated sections, was not grading, but an oldstyle (with large x-height and short descenders) that has robust micro-detailed serifs and fine tapered joints; that way, large amounts of press gain are accomodated on the glyph as a whole, yet the details prevail when printing is finer.
Historically, Fortune magazine in the 1930s had both coated and rag pages, set in Baskerville. The difference in effect was ridiculous, but so what?
Corel users weren’t the professional graphic designers who constituted the market for quality fonts at that time.
Here are the freebies which were bundled with Illustrator in 1993.
Perhaps it was a response to other players (including Apple), but I suspect that the applications departments at Adobe didn’t realize they were negatively impacting the type department, and were enthralled by the idea that suddenly they no longer had to cram their apps onto floppies, but had CDs with lots of empty space on them, and that filling it with free fonts would enhance the user experience.