Nothing has changed since they started enforcing the TM30 law in 2016. The only time you need to update is if you have been overseas and even then - you show your previous slip in your passport, they stamp it, record your new TM6 and you're on your merry way.
in theory you should be fine as you're getting the right visa, that said, there was this story on Thaivisa the other day, guy got hassled even though he did have a Non-Imm O but in context he'd had a lot of recent entries.
I get some of the skepticism here given where the first reports of a massive crackdown by Vientiane came from a couple of weeks back, but are we close to admitting that Vientiane is no longer the happy/easy place to get tourists visa from yet?
Op- you need a multiple re-entry permit. To others - I'd note that the 24 months is dated from the day of work permit application, not the day you get the work permit, at least it was in my case. Depending on your office, the processing time might be over a month give or take. Your extension of stay based on the initial 90 day Nom-Imm B (BOI) visa is then dated as the same day your work permit expires. In my case it was 22
Do when you please, both single and multi-entry are stamped as valid to the same expiry date as your visa, the single obviously only being valid for one use.