a) If a certain fruit has more than one “season” per year, does one make a new shechiyuna on the fruit each season or yearly? For example, let’s say grapes have 2 seasons in 1 year, should one say a shechiyanu twice in that year even though the fruit isn’t really new at all to me and in fact I am still eating the fruit from the previous season when the new season arrives?
b) Today, certain fruits can be found in stores all year around, due to freezing facilities, and imports from abraod. Should one ever make a shehichyanu on fruit that are found in stores all year around, regardless of the new season?
If a fruit has two seasons in one year, one should make a shehecheyanu twice (Mishnah Berurah 225:17; according to Kaf Hachaim (225:42), one recites the berachah only once a year). However, if the fruit is present the whole time (at the same level of quality), so that the “new season” cannot be noted, no shehecheyanu whatsoever is made. This is usually applicable only to those fruit that grow more than twice a year (Shulchan Aruch, Orach Chaim 225:6). If the fruit are available during the entire year (by means of refrigeration), and their quality is more or less equal to that of fresh fruit (based on Aruch Hashulchan 225:12), one shoud not make a shehecheyahu, but it is correct to make a shehecheyanu on a different fruit (or new clothing, etc.), and have in mind both fruit (see Rema, loc. cit.; see also Iggros Moshe, whose leaning is that one should recite a berachah, yet concludes that perhaps it is correct to minimize berachos; see Vezos Haberachah, p. 169, who writes that one should not recite a berachah, but adds that a berachah should be made on other fruit).