My
Barber dimes I bought in bulk from an estate sale and
ebay, so I am not as familiar with them.
The set that I am most familiar with are the quarters. One thing I've learned is that seemingly random dates will plague you. Of course there are the "Big Three" as mentioned that are extremely pricey and pretty much
only exist in AG-01 to F-12 grades. Hopefully my experience will provide you with some insight. I am putting together a VF-XF set, and am up to 66 of the 74 total in the series. I attend the Long Beach coin show at least twice a year, monitor
ebay, and make my rounds of local coin shops in the Los Angeles and Orange County areas. So far, it has taken about two years of diligent collecting to get to the 66.
Besides the "Big Three," other dates that have escaped me are the 1892-S, 1895-S, 1897-S, and the 1906-O. I have run across a handful of pleasing examples of the 1909-O certified VF-20, but unfortunately at the time cost was a factor.
One thing you will need to know is how to grade both sides of this coin. The Barber "cheat" method is to just check which letters of "LIBERTY" are visible to determine the grade. But weak strikes can mean that a coin missing the lower band line and have weak lettering may still be a VF-quality coin when inspecting feather and arrow detail on the reverse. Of course always strive for coins with stronger strikes -- but oftentimes you won't have that option with how low the survival rate is of certain dates/mints.
I'm trying to do some due diligence on the half dollars. I have about 20 later dates in VF condition, which is a good start. But I imagine that set will take longer than the quarters and ding the wallet just as much.