I know (at least in Europe) if you travel with children it can be a good idea to take a birth certificate and permission of the other parent if you travel alone with the child. They never asked me, but they can if they suspect child abduction. I travelled a couple of times alone with my Thai daughter (baby, she has my family name) and was never asked anything. This was in Bangkok and Phuket.
You visited Thailand only once a year. I was once questioned. I entered Thailand for the third time in a year with a VE. The first 2 visits I also extended the "visa". But even that third time they let me in after I told them the reason why I came.
Outlook is bad. Not only for the Thai pass. Microsoft was never able to fight spam like Gmail so they decided to refuse email from new domains or put all email from new domains in the spam box. So when Thailand comes up with something new and sends email from a new domain it will often not arrive or it will arrive in the spam box. If you are serious about email you should avoid Outlook.