That's not that bizarre. It's not just Wind or Chatr either. It's quite common to have text messaging problems after porting, ESPECIALLY text mesages originating from the old carrier. Most people don't have these problems but it shouldn't be a huge surprise when it comes to text messaging. Many times, this problem resolves itself automatically over time. There have been many example on this site where people's services would work fine with the exception of text messaging from the old carrier until the start of the next billing cycle of the old provider.
I had a problem with Wind before when I ported out to another company (have since gone back to Wind) where the number got ported out but Wind somehow forgot to close the phone line/account out, even though service was fully transfered to Rogers at that time. Wind service continued to work, but despite Wind assuring me that porting was complete to Rogers and that I wouldnt' be charged any longer for Wind services, they kept the line active and continued to bill me until I complained about it. Making calls from the Wind phone (which was supposed to be cancelled at time of port out) to my phone number rang on the proper Rogers phone but text messages from that Wind phone to my phone number got delivered to my same Wind phone. I suspect that all text message from any Wind customer were also incorrectly staying within the Wind network but at that time, I just didn't care about that part because this was 1 month after Toronto launch and quite honestly, back then almost no one was using Wind. The entire time, the phone number porting databases clearly listed my phone no longer being with Wind.
Check if your Wind phone actually still works. Talk to Chatr and Wind about it but be warned - expect a lot of run-around and lots of finger pointing by those 2 companies at each other.