Thing is you already shown your proof of income etc during the extension of stay application for retirement, marriage etc. So having a re entry permit based on that is all good. I have been in/out with no hiccups past years.
Overstay is overstay. No ifs and buts about it. It’s already a big mistake on OP’s part. But the question is about can he re enter again that’s about it. So stop being long winded and judgemental.