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ש Shin/Sin - 21st letter - Gematria 300

ש is peculiar in that it has 2 equal pronunciations, as SH or as S in English. When it is pronounced as S it has exactly the same phonetic value as ס (Samekh).

The reason for these 2 different pronunciations is not known to the modern simple man. Maybe TLS with its claim of 5,000 years of unbroken history knows? If so, could they share that secret with us as well, please?

In Aramaic ש is pronounced as SH.

Peace (or Hello, Goodbye) in Hebrew is שלום (Shalom). In Aramaic is שלמא (Shlama).

A common word that starts with ש pronounced as S is שׂמח (same'ach), meaning Joyful, Happy. 

ישראל (Israel) is also written with a ש (Sin) not a ס (Samekh) in Hebrew.

When dots are added to the consonant word skeleton, to indicate vowels, begadKephat value, doubling of consonants or to distinguish between Shin and Sin, a dot is added to the right to indicate a Shin sound, like in שָׁלוֹם (Shalom). And a dot is added to the left to indicate Sin, like in יִשְׂרָאֵל (Israel)

ר Resh - 20th letter, Gematria 200

In Modern Hebrew, ר is pronounced as R in French, Danish, etc. Some pronounce it also as a rolled R, the way it is pronounced in Aramaic, Arabic and Romance Languages. Even if you pronounce it as an English R, you will be understood.

But what can beat the fancy of a French R? If you can pronounce it as a French R, your social standing will immediately shoot up in Israel :-). Modern Hebrew, these days, sounds more like a European language, not rough and harsh, as other Semitic languages like Aramaic or Arabic sound to the ear of a Westerner. But rest assured, in history Hebrew sounded more like Arabic/Aramaic. It did not have the European sound and feel it has today.  Hebrew grammar is also totally Semitic, similar to Aramaic or Arabic.

The word רב (Rav) in Hebrew means "Rabbi" or "great/many", depending on the context.

In Aramaic רבא (rabba) means "great". רבי (Rabbi - pronounced Rabbee, not Rabbai) means My Great One, which is the literal translation of the word Rabbi. Rabbi can also mean My Teacher, My Master, etc.

Note that according to Sepher Yetzirah ר is also considered to have double pronunciation, bringing the total number of consonants like that to 7.  Maybe we should say begadkepherat instead of begadgephat. But that second pronunciation is not known to the common man these days.  Again, maybe TLS does?

ק Qoph, 19th letter, Gematria 100

In Modern Hebrew, ק is pronounced exactly like the primary sound for כ, as K in English.

In Aramaic, ק is pronounced as a K that is vocalized deep in the back of your mouth. The sound ends up being a bit different than כ.

The Modern Hebrew word for Monkey is קוף (Qoph). In Aramaic is קופא (Qupha). Fancy me.

צ \ ץ Tsade, 18th letter, Gematria 90

צ is the last letter of the set of 5 letters that has a different final (end of word) form ץ.

In Modern Hebrew, צ is pronounced as TS in Tsunami, or Cats.

In Aramaic צ is pronounced like an S sound between S and TS. Get your mouth ready to say TS, but vocalize an S instead, keeping your tongue like a rounded cup against the edges of the roof of the mouth. That's צ in Aramaic.

In Hebrew a rightous/holy person is called a צדיק (tsadik). In Aramaic is צדיקא (ṣadiqā). I am guessing TLS calls Rabbi AA a צדיק.

פ \ ף Pe, the 17th letter, Gematria 80

פ is the 4th letter of the set of 5 that has a different final form ף, and it is also part of the BegadKepahat group of letters that have a secondary pronunciation. The secondary pronunciation of P is F, in both Modern Hebrew and Aramaic.

Like with Abraham/Avraham in the case of ב (Bet), one could find Semitic words imported into other languages spelled with either P or F, because the consonant is פ but the pronunciation is F.  E.g.  Yosep/Yosef. 

The word for Mouth in Modern Hebrew is פה (Pe). Fancy that one too.

ע Ayin - the 16th letter, Gematria 70

ע is a hard letter to pronounce for speakers of non-Semitic languages, if the Aramaic pronunciation is to be used.

Modern Hebrew has made it easy, by simply pronouncing it as א (Alef), when not immediately after a consonant or at the end of a word. In such cases, like א, it is silent in both Modern Hebrew and Aramaic. 

In Aramaic, ע is pronounced like an א (Alef) deeper in the throat and with the throat constricted, as if an invisible hand is choking you. It is pronounced as Arabic ﻉ (Ayin), usually the less rough version of it. Some Jewish people will still pronounce ע like in Aramaic, even in Modern Hebrew.

The word for Eye in both Modern Hebrew and Aramaic is עין (Ayin). Fancy that.

ס Samekh, the 15 letter with numeric value of 60

ס is pronounced as S in both Modern Hebrew and Aramaic.

The word for Horse in Hebrew is סוס (Sus) while in Aramaic is סוסא (Susa).

Note: In all the transliterations, the Latin not English transliteration is given.  As such the U in Sus is pronounced as Soos in English.