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Answer: There are various credible minhagim on these matters. We will mainly explain the issues, although we will show mild preferences for certain practices for those who lack a clear minhag.
The gemara (Kritot 6a) says that since symbolism has significance, one should "be in the practice" of eating (some texts – "seeing") certain foods (dates and four vegetable simanim) in the "head of the year." While some say that "being in the practice" refers to all Rosh Hashana meals and some say that it is only for the year’s first meal, the more accepted practice is to eat the simanim at both night meals (see discussion in Mishneh Halachot XIII:80; Torat Hamoadim, Yamim Noraim 4:1).
The more prevalent minhag (in homes and among poskim) is to eat the foods after Hamotzi (see Tur, Orach Chayim 583; Magen Avraham 583:1; Taz 583:2). Besides the logic of eating the foods during the meal, some poskim claim it solves a halachic problem (see Torat Hamoadim ibid. 2). If one eats them before the bread, we have the same question about needing a beracha acharona as after eating karpas before matza. While we solve that problem by eating less than a k’zayit of karpas (see Shulchan Aruch, OC 473:6), many people want to eat more than ak’zayit (combined) of the simanim.
Actually, eating the simanim after bread raises other berachaquestions. The poskim assume that one makes a beracha rishona on the fruit simanim even though it is during the meal, which is not simple. While fruit eaten for desert requires a beracha rishona, fruit served as an "appetizer" gets no beracha (see Mishna Berura 174:39; V’zot Haberacha, p. 77). Perhaps the fact that it is eaten for ritual, not culinary, reasons is a contributing factor to justify a beracha (see Divrei Yatziv, OC 252).
A related question is whether to recite Borei Pri Ha’adama on a vegetable siman. As a rule, we do not do so on vegetables during a meal, as they "accompany the main meal." In our case, there are varied opinions. The more common practice is to make the beracha, perhaps because they are eaten as simanim, but some argue that this makes no difference (Teshuvot V’hanhagot II:269; Torat Hamoadim, ibid.). Some (see Halichot Shlomo, Moadim II:1:18) compromise by saying to make the beracha on the least "normally eaten" of the vegetables, which some assume is kara (gourd family). (Piskei Teshuvot (583:(13)) cites Rav Diblitski as suggesting a safe although unnatural idea – first eat from aBorei Pri Ha’adama fruit (e.g., watermelon, banana), which certainly requires a beracha.)
Another question of minhag vs. regular rules of berachot relates to the order of berachot. When one plans to eat multiple fruit, he makes the Borei Pri Haetz on a fruit of "the seven species" (including dates and pomegranates, in that order, based on their order in the pasuk – Shulchan Aruch, Orach Chayim 211:1,4). Yet, the common minhag for Ashkenazim is to eat – with a beracha and Yehi Ratzon – the apple dipped in honey first. (It is hard to know how the minhag developed. Is the idea of "shana tova u’metuka" more central (even though it is post-Talmudic) and warrant precedence?) Some take the purist approach, making Borei Pri Haetz on the date, and have the apple later (Halichot Shlomo ibid.). A way to keep the order of the Yehi Ratzon yet follow the regular rules of berachot is to have the dates and pomegranates off the table, while having them in mind, when making the beracha on the apple (ibid.). One can also make the beracha on the date, eat a small amount, then eat the apple, pomegranate, and date with the order that fits hisYehi Ratzon preference.
Despite contrary common practice, poskim recommend taking a small bite from the food(s) that gets a beracha right after the beracha, with theYehi Ratzon being said before further eating (Mishna Berura 583:4).
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