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Interesting. I've only had a short glimpse a Unger's paper. Does "$\mathbb P$ is absolutely $\delta$-c.c." mean that $\mathbb P \times \mathbb P$ is $\delta$-c.c.?
Zetapology, that's actually not an issue. It's just that $\beth_{1}$ represents different ordinals in different models. If we fix the ordinal $\alpha$ - not the definition $\alpha$ may satisfy - as I did, everything works.
@Goldstern You're right, of course. I'm not entirely sure how to elegantly state what I have in mind but something like "for every $\alpha > 0$ there is some forcing $\mathbb P_{\alpha}$ such that $1 \Vdash_{\mathbb P_\alpha}^L \neg \mathrm{CH}(\aleph_{\check{\alpha}})$" would work. However, I don't think that focusing on this formality is very helpful to OP which is why, grudgingly, I consider keeping my statement as is.
Note that if we relax the phrasing of the first question a bit, we can get positive results: Let $U$ be a 'sufficienlty nice' measure on $\kappa$ (e.g. be derived from an ultrapower embedding) and let $i_U \colon L \to L$ be the restriction of the ultrapower embedding to $L$. This itself is an ultrapower embedding of the structure $(L; \in, U \cap L)$ (i.e. definable in this structure by the usual construction) and in there $i_U(\kappa)$ is weakly compact.
Can you give more details? What exactly is your definition of a game? What is a turn? What are the winning conditions? What is the pay-off? In its current state you can easily construct a 'game' in which this approach will fall flat. Simply let a given player lose if he follows your proposed strategy.