So, i was thinking about one interesting aspect of start date: Civil War of 1425-1453 (it is known in english sources as Great Feudal War and Muscovite Civil War).
Cause practically all main participants has similar names, here are references to names:
Vasily II, oldest son of Vasiliy I and grandson of Dmitry Donskoy -
The Blind (he is not blind at the start of the story).
Yury Dmitrievich, third son of Dmitry Donskoy -
The Pretender.
Vasily Yrievuch, oldest son of Yury Dmitrievich -
The Squint.
Dmitry Urievich, second son of Yury Dmitrievich -
The 3-4-3 or
The Shemiaka (we don't know how he got this nickname, but there are two main theories - first it is from tatar word for rich outfit, jewelry; second is "someone who can give a good beating", strongman).
First part, where
The Pretender and his sons beats crap out of
The Blind.
1389: Dmitry Donskoy in his will apointed his third son, Yury Dmitrievich(
The Pretender), as heir to his oldest son, Vasily I Dmitrievich. So, after death of Vasily I, Yury could claim Great Duchy bypassing Vasily II (
The Blind, son of Vasily I).
1428:
The Pretender aknowledge his nephew
The Blind as "eldest brother" therefore losing his claims on throne.
1431:
The Pretender tries to get yarlik (right to rule) from khan, but yarlik goes to
The Blind.
1433: During
The Blind's wedding his mother, Sophia, tore off golden waistband from
The Pretender's son
The Squint (this waistband was allegebly given to Dmitry Donskoy as dowry during his wedding with Evdokya Dmitrievna, but was replaced by one high-ranked general and through marriages got to
The Squint, the whole story considered fake so they would have reason to deal with one traitor and insult Yury).
So, sons of
The Pretender decided to go to father to Uglich plundering Yaroslavl (patrimony of Vasiliy II) on their way. Obviously
The Pretender sided with his sons and defeated army of Great Kniaz
The Blind on Klyazma.
The Blind ran to Tver and, after, to Kostroma.
The Pretender gave to his nephew (
The Blind) principality of Kolomna and started to rule in Moscow. But boyars and service class people (people who served to state in administration or army) weren't really into Yury, so a lot of them ran to Kolomna. Both sons of
The Pretender also joined
The Blind in Kolomna, cause they quarelled with father. So,
The Pretender decided to step back and give throne to
The Blind again.
1434: Repressions towards older rivals of
The Blind, that followed, forced sons of
The Pretender to fight. They defeated
The Blind at river Kus'. Later
The Pretender himself joined, cause Great Kniaz forces sacked Galich. And, again,
The Blind was defeated (under Rostov).
The Pretender, again, took Moscow, but died soon (at that time people believed that he was poisoned) and bequathing throne to
The Blind.
This looks like gangster wars, but all those feudal wars were like that lel.
Now, to the next part, where
The Blind beats crap out of
The Squint and gives him such nickname.
1434:
The Squint doesn't want to accept this situation and declares himself Great Kniaz, his brothers didn't support him and concluded peace with
The Blind (
The Shemiaka got Uglich and Rzhev, third son of Pretender got Galich and Bezhetsk). When armies of those approached Moscow,
The Squint took his father's treasury and escpaed to Novgorod.
After month and a half in Novgorod,
The Squint went to Zavolochie, then to Kostroma, after which he went with army to Moscow.
1435:
The Squint was defeated on river Kotorosl near Yaroslavl (i think you see, who was THE GENERAL in their family ( ͡° ͜ʖ ͡°)). He escaped to Vologda.
1436: In Vologda he gathered new forces and marched on Rostov, during which he took Nerehta (pretty rich city, which was razed in 1609).
The Blind concentrated his forces in Rostov.
His ally, knyaz of Yaroslavl Alexander Fyodorovich, was defending - guess whoch city - Yaroslavl from part of
The Squint's army. But he lost and was captured with his wife. Huge ransom was payed, but they were released much later.
The Squint wanted to surprise
The Blind, but the latter leaved Rostov and took position in the way to Rostov.
The Squint was defeated on river Chereh 14th may 1436. He was captured and blinded, after that he got his nickname (hint - the squint).
The Blind then released
The Shemiaka, which was kept in captivity in Kolomna. All lands wre returned to the latter.
1440:
The Shemiaka inherits his youngest brothers lands (Bezhetsk and Galich).
Third part, in which it all comes to the conclusion.
1445:
The Blind was defeated and captured after his defeat under Suzdal to khan of Kazan - Ulu-Muhammed. Because of traditional inheritance -
The Shemiaka became new Great Kniaz of Moscow.
The Blind, freaked out, promises ransom to khan, gets army and marches to Moscow. In this case, practically all people (including merchants, boyars, clergy etc) supported
The Shemiaka - they were outraged by "horde general"
The Blind.
1446: With help of those dissatisfied with
The Blind's behavior -
The Shemiaka becomes Great Kniaz. With help of former supporter of
The Blind, Ivan Andreevich of Mozhaisk, they were able to capture
The Blind during church service, which the latter visited in Trinity Lavra os st. Sergius (this monastery is dedicated to st. Sergius, who blessed Dmitry Donskoy on battle with tatars).
The Shemiaka accused
The Blind in cooperation with tatars and blinded him (also, this was also revenge for his brother -
The Squint). So
The Blind was sent to Uglich and, then, to Vologda. But, after some time, a lot of dissatisfied by
The Shemiaka started to com to
The Blind. Among most noticable are: Boris Alexandrovich, Great Kniaz of Tver; Vasily Yaroslavovich, kniaz of Serpukhov-Borovsky (territory between Tula, Kaluga and Moscow); Alexander Fyodorovich, kniaz of Yaroslavl; Ivan Ivanovich, kniaz of Starodub; and a lot of others. On 25th december Moscow was taken by army of
The Blind while
The Shemiaka was absent from capital.
1447: On 17th February
The Blind entered Moscow.
The Shemiaka was near Volokolamsk at that moment, so he decided to retreat. First, to Galich, then - to Chuhloma. He was continuing fighting
The Blind.
1447-1449: Standstill. During this time
The Blind stroke deal with Casimir IV, which confirmed border between Lithuania and Muscovy, both parties agreed not to support internal enemies of each other, also Casimir gave up claims on Novgorod and Pskov (Tver stayed in sphere of Lithuania, but not for long, and Rzhev was given to Tver), Ryazan and Tver were devlared "free to act as they want", Verkhovskie Knyazhestva (Odoyev) stayed in sphere of Lithuania.
1450: On 27th January
The Shemiaka was defeated under Galich. Then - under Ustyug.
1452:
The Shemiaka was surrounded by armies of
The Blind, lost his domains and escaped to Novgorod. There he died in 1453 (rumoured to be poisoned by supporters of
The Blind).
1456: Treaty of Jazhelbitsy was stroke, in which Novgorod practically lost its independance;
So, what we see from those events:
1) Shemiaka shouldn't be general (i can find another name, if you need, cause there were a lot of good generals);
2) Vasiliy II was GREAT diplomat and administrator, but poor general, still 3-1-2, so he should be buffed to 3-3-2 at least;
3) seriously, losing Moscow so many times...
And a little bit about Treaty of Jazhelbitsy. There were two different documents - one for Moscow, one for Novgorod. Both were different.
Document for Novgorod had this important points:
1) Novgorod couldn't have its own foreign affairs and pass laws;
2) Grreat Kniaz became "supreme court" for Novgorod;
3) Signet of Veche and its appointed mayors was replaced by signet of Great Kniaz;
4) Novgorod shouldn't give shelter to enemies of Vasiliy II.
Most of points were respected by both sides. But Novgorod still gave shelter to enemies of Knyaz and Vasiliy resolved trials in favor of muscovite boyars, who got domains in Novgorodian land through this.
So, maybe, instead of conquering we should give quest on vassalization? Not sure thou. It is like with Mamluks in the end - whole state was annexed after in one war. But, with some good decisions, you should be able to maintain good relations and integrate Novgorod.
Also, idea - adding Volok Lamsky. This will split Kaluga in half, but will represent importance of the city which stand on trade route from Ryazan and Moscow to Novgorod, had a lot of stone buildings (including frotress with big mansion - whic represents its wealth) and was one of the strategic points between duchies of Novgorod, Tver and Moscow. It also was capital of specific principality during reign of Vasiliy II.
To the contents.