First of all let me say the story was well written and I enjoyed the journey. It also was pretty funny.
However I am conflicted because there were a few details that the author put in that made some of the MC’s Major choices stupid, and would have only been understandable if he were a teenager instead of an old man. I also think that those details were put in simply to ‘raise the stakes’. I’m not sure how to describe it without actually doing any spoilers so I will make an example that happens basically at the very beginning, so it shouldn’t be a spoiler if it was obviously the choice that was made.
In case you don’t want any chance of spoilers stop here
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He is told that if he transmigrates he won’t be able to have an afterlife or anything like that, which means if he’d think about it he would just stay dead because when his wife dies she would come right back to him, I mean he died so no big deal, especially since his wife died already too. But because of this choice it basically means he will only be with his wife in this next life for the short time they are both alive. It just seems like a waste. This also means that another choice that he deliberates on (but I don’t think he has decided yet) is going in the same direction but even more strongly, and that one I feel that making it would make his wife disgusted with him, considering how he’s described her, yet unless he is going to spend his life lying to her (lying MCs are actually the MCs I hate most, being weak willed or even an ass is fine as long as you are honest about it), I would think that he would try to act in a way to make her happy with him.