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eastcoastceojam

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If you don't mind cheesing things, the advice in the HOI4 wiki is pretty straightforward:


https://hoi4.paradoxwikis.com/Achievements
Second Time’s the Charm - Can be done easily if siding with Germans. Rush the monarchist focus tree, you need "Avenge Waterloo" focus. Prepare to attack Britain with naval invasion. Your starting army and fleet will be enough to destroy them. Wait until Germany declares war on Poland. Britain will join the war. The moment they do this declare war on Britain. Germany will invite you to their faction, accept this invitation and annex Britain. Guarantee Finland as the USSR justifies a wargoal on them. Accept the call to arms and invite the rest of the Axis. This will make the war easier as they will not receive the "Great Patriotic War" buff. Once they take Moscow, ask them to give you control in that state. Make sure you have enough warscore so they will allow this.
 
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Blizzard Six

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I got this by going to war with Germany in 1938 over the Sudetenland. Czech and Romania enter a faction with you and the three of you can handle Germany, especially if playing non-historical and Italy isn't in the Axis (they probably won't be in the Axis by 1938 anyway). Then I guaranteed independence of Poland and when USSR invaded them in 1940 or so Poland joined the faction with us and I was able to defeat USSR pretty handily. I naval invaded through Leningrad and pushed to Moscow for the achievement, but you can also request control of it from an ally if they happen to occupy it first.