I also switched from Non-O Retirement to DTV shortly after it came out. I applied through Vancouver consulate and was approved a couple of hours after I applied. Crazy fast! Wife was approved for her DTV the next morning as a dependent on mine.
A few months ago my BKK debit card expired. I had to go in to the bank with my passport and get a new card. They saw I was on a DTV and it was no issue as I've had it for a few years now and got it while on the Non-O Retirement and haven't use an agent for anything in Thailand.
I'm on the workcation type of DTV as I'm a business owner in Canada. I was a self-employed software engineer who retired in 2017. Now I just manage my Canadian company's finances (that we live off) with calls, emails and limited online meetings over things like taxes, corporate registration renewal, corp. investments etc. No more software development but it's enough work for a workcation DTV.
We've come through customs multiple times with the DTVs and had no issues at BKK or CNX. The big reasons to switch were no 800K x 2 needed to sit in Thailand beyond what we need to live off (Canada just stopped issuing affidavits of income), no visits to immigration and multiple entry for 5 years. We come and go fairly regularly so every time we enter we get a fresh 180 days.