First pics are better because in these pictures there is glare on the bust and hair which makes it harder to see wear and detail. A key feature on Barber's is the LIBERTY band on the bust so if anything try to get a close up view of that and/or the hair detail. Since this is a pre-1901 Barber half I would say (and I'm a novice so take it with an unusually large grain of salt) the line under the LIBERTY band needs to be raised and complete to get the XF-40 grade. Otherwise it is a very solid VF35.
I would suggest sending your coins to PCGS or NGC instead of ANACS. First of all coins certified by PCGS or NGC make more money than ANACS, so even if its more expensive its worth considering. Second ANACS is known to slap "CLEANED" on many of their slabbed coins which will murder the market value of your coin (or just waste your time & money for the grading).
Quote:NGCcoin.com: Barber halves pre-dated the popular collecting of coins from circulation, which began during the mid-1930s. Though most of the dates after 1900 could still be found with some effort at that time and for a few years afterward, these coins were by then quite heavily worn. Thus,
Barber halves survive primarily in grades below Fine.
In fact, the grades of Fine through Extremely Fine are those most scarce and highly sought by date and mint collectors. Examples having their natural surfaces intact ("original" is the popular term) are always in high demand.