I think the show is pretty solid. It does a good job of showing him being beaten down by trauma and how the experiences of his past life shapes his current thinking and how he approaches certain situations and how he eventually overcomes them with the help of others.

A lot of isekais just have the characters reincarnated and then they just forget their past lives and move on. I think Jobless does a good job of reminding you that this is his second chance.

Nah, if anything you'll get more of his original round appearance in the mindscape bits (because that's how he still views himself, despite moving to a new body). You can also look forward to erectile dysfunction being a serious plot point.

pick it up. it gets less weird because he gets older, just keep in mind that although he's technically in his 40s, he's socially mature enough to be a teen, so it all kinda equals out.

my favorite part of the whole story is watching him go from "I know more than these assholes" to "I have no idea wtf I'm doing, why did I do that?!"

highly recommend the series, however you should probably avoid the manga as one of the chapters has been banned in the US for "stuff".