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in Serbia, Medvedev's name is spelled as Mедведев rather than [Meдвједев], but Dostoevsky's is spelled as Достојевски.

All three "E" in Medvedev and Dostoevsky are gliding E, because any "E" in Russian glides a bit. If you don't glide it at all, it is spelled with Э, or is a foreign word, like "integral".

If you speak in Russian and don't glide your E's, you speak with an accent but you will be understood. Some foreigners overglide (if that's a word), and that is an accent too. There is an episode in one of the two satrical Ostap Bender novels (12 Chairs or The Golden Calf) where Ostap sets up a phony enterprise using a typewriter that has its E hammer broken, so he substitutes Э for Е. That typewriter is hilariously described as "typewriter with a Turkish accent".

There is something in E following an O that prevents the tongue from naturally glide, so you would want to put a Y in Dostoyevsky.

I don't know if there are any firm transliteration rules in English about Russian E; there probably aren't. People insert or omit these Y's based on what they see others do, or upon their own intuition.

Short-long distinctions do not exist in Russian (or Bulgarian). Vowels are lengthened for emphasis. "Лук" is pronounced the same in either sense. I did not know that they existed in any Slav language, thank you for telling me.

Yat, "Ѣ"

This topic is so obscure, even finding Ѣ in Unicode was hard. So far as I can tell, by the time the letter was abolished there was no discernible phonetic difference between Ѣ and E in Russian. I do not know the old spelling rules (I am generally not a linguist). I have a suspicion that where in Bulgarian there is a dual pronunciation Е/Я (беха/бяха), that reflects "Ѣ in some way, but I do not really know. See this article for more: Yat; it mentions some other letters that were dropped even earlier.

Святой, etc., also reflects that duality in Bulgarian. In modern Russian, however, only Я is used as far as I can think of it: священник, святость, посвящение. In Bulgarian, E is used in all words corresponding to these.

Alex, what do you mean by "gliding E?" That said, Serbian pronunciation of E is exactly equivalent to Э. Thus, when the Serbs see Медведев, they read it as Мэдвэдэв. I believe the Bulgarians pronounce E exactly the same, as an Э. To my ears, the unaccented Russian E is "softened," not a full YE but rather as if it had a Ь in front if it. On the other hand, accented E tends to be more like YE.

There is something in E following an O that prevents the tongue from naturally glide, so you would want to put a Y in Dostoyevsky

In Serbian, лук (onion), is identical to the English "look" (although it is a double "oo" it is pronounced as a short vowel). On the other hand, лук (bow), as in "лук и стрела," the "y" is distinctly long but not quite double "уу."

But you won't find a Serbian linguist who will tell you that there is a long-short distinction, but it is clear as a bell to anyone with half way decent hearing.

Another distinction that is actually sometimes made obvious graphically is "a," such as in the genitive case of "letters" (писамâ) or "in order to give" да дâ.

I seriously doubt that similar differences don't exist in other Slavic languages, including Russian and Bulgarian. They may not be recognized, but they must exist, for all vowels can be pronounced as long or short; In Serbian кост, мост, со(л), etc. are long "o" sounds, while боље, кољиво, коњ, слон, etc. are all short "o" sounds.

This topic is so obscure, even finding Ѣ in Unicode was hard

It is obscure in Russian and Bulgarian, which is why it was eliminated. But eliminating it in Serbian was a major mistake. In Serbian the palatalization (inflection) of Ѣ is a major factor in the division of standard Serbian into two geographical variants, which is why Ѣ was a perfect solution for a unified orthographic standard. Today, many refugees from the western parts of the former Yugoslavia bring with them their western version of the language into Serbia and confuse the kids there.

As said previously, this difference is not trivial. Thus победа is pronounced as побъеда in the western dialect but as побэда in the eastern. The word used to be spelled uniquely as побѣда, but today it is spelled побједа and победа.

But how is святость pronounced in Russian? Isn't is more like svetost' than svyatost'? Why not replace it with a "gliding" E then? :)