If I understand, I believe his main concern is what could the repercussions be if he were to ask for a supervisor.
That choice is up to you. I doubt that the IO is looking to harm you, it could be that they do not know the exact rules and a supervisor should either be able to explain why the police clearance is needed, or scrap it all together?
Edit: and take your wife, so there's no language barriers.
You will if that's where you're staying. Head to your immigration and pick up a form, it will contain all the documents required for that immigration office.
I believe there have been conflicting reports and a lot will depend on which immigration office you use. Your best bet is to go to your immigration and ask. At best, you get the extension, at worst nothing changes.
Unfortunately VFS Global have pretty much gone radio silent and the UK embassy isn't addressing the situation either at the minute, so it's just a waiting game.
Noted and yes, the only difference between the 60 day and yearly extension was the financial requirements and also a hand drawn map from the immigration office to your residence.
Noted on the virus, I had seen some questions about whether you can go to get your extension early, in the case of Songkhla you can.