Tzadik Gamur / City People

1. Tzadik Gamur - The gemara says that a known rasha who is mekadesh a woman on condition that he is a tzadik gamur, we are choshesh for his kiddushin (Ran) because maybe he had a thought of teshuva. Similarly, if he is a known tzadik and is mekadesh on condition that he is a rasha, we are choshesh that he had thoughts of avoda zara (which the gemara said on 40a that Hashem considers like a ma'aseh). The minchas chinuch (164) struggles with this gemara, based on the premise that teshuva is a process that requires many steps including viduy, so a thought of teshuva should not be sufficient to render someone a tzaddik. To answer this he says a tremendous chiddush, that the steps of teshuva are necessary to achieve atonement, but to change one's status from rasha to tzadik, all that is needed is a thought of teshuva to not do any more aveiros from now on. Based on this, it should follow that the thought to do aveiros starting from now should render a person a rasha even though he has many zechuyos for past mitzvos. But by aveiros Hashem doesn't consider thoughts to be action, and that is why the gemara says he would only be turned into a rasha by a thought of avoda zara. The gemara didn't want to say that he can be turned into a rasha by having charata on past mitzvos (as it says on 40b), because that may take aways his zechuyos for the past but won't render him a rasha.

2. City people

The mishna says that if he stipulates that he is a small city person or large city (krach) person, and he is the opposite, then the kiddushin is void. Rashi explains that even if he is actually a small city person, and he stipulated that he is a large city person which is a change for the better, the kiddushin is void. The maharsha asks on rashi that in the gemara earlier when we were trying to prove that R' Shimon's silence in the later mishnayos implies that only a change for the better in monetary issues would be a valid kiddushin (not a change in guf), from the fact that R' Shimon doesn't argue in our mishna about the kohen, levi, mamzer. The gemara then asks that he also doesn't argue in the mishna later about having a maid which seems to be a monetary issue. Why doesn't the gemara ask from this earlier case where R' shimon doesn't argue even though it is a monetary issue. Based on this the Maharsha disagrees with Rashi and says that a small city is not objectively better than a large one, nor is the opposite true, but different strokes for different folks (a large city has more amenities but also more noise). That is why R' shimon agrees, because there is no objective better and worse. Perhaps we can be meyashev Rashi based on the Rashash, who points out that this issue is listed together with "guf" things, such as kohen, levi mamzer. This implies that the issue is not whether he presently lives in a large or small city, rather where he was raised because it would have a definite impact on his personality. Now, even if Rashi is correct that an small city is better than a 'krach', R' Shimon would not argue since these are changes in his guf, not a monetary change.