Looking back from my Ivangorod Prosperous TL that I had written last year, it featured an early rise of Russia's mercantile port of Ivangorod and its effects in the Baltic, mainly butterflying away the Livonian War and increased contact between Muscovy and England. IOTL, Ivangorod was neglected because Hans Schlitte was caught in Lubeck by the port authorities on Poland's request. (This is the PoD I chose for Ivangorod Prosperous)
IOTL, Poland-Lithuania and Sweden became allies against Muscovy in the Livonian War, resulting in Russia's defeat and proved to be extremely costly. Now the real question is:
1) If the Livonian War did not occur and instead, Muscovy focused on waging war against the three remnant Khanates (Kazan, Astrakhan and Crimea) and making an attempt to conquer all of them instead of the first two?
2) Where can Russia's first spot for a port be located if they gained access to the Black Sea instead of the Baltic? Could the fortress of Azov be the first stronghold that the Muscovites can conquer?
3) Is the port of Arkhangelsk the perfect port for an earlier Russian expedition to Siberia and beyond, combined with the Mangazeya colony that still survives?
4) If Poland-Lithuania and Sweden remain allies even during the Times of Troubles in Moscow, then which country can ally with Muscovy since it is literally surrounded by enemies from all sides?