Markst
I am retired also, living alone here and never had any problems to get an O visa. You just have to proof an income of 800000 baht or more per year.
I only have to cross border every 3 months, get a new stamp for another 3 months, thats it.
Anyway, I prefer to receive the 1-year visa during my yearly >vacation< in my birth country at the nearest Thai consulate there. You even dont have to pass by, but can do it in writing.
As I heard getting a working permit is 800000 baht per year also.
So it seems to be a matter of money only.