maybe better to just deal with the curent trip, and wait to see what the rules are before dealing with 2nd trip... requirements change all the time.

a few months ago 1 way to PP was $75USD

I was there only a few months ago. It was then recommended and suggested that ED was only being approved when already in Thailand. i.e. Language and Thai boxing. Visa exempt is only 30 days but can get 30 day extension while applying for ED visa, but you would want to start that right away and not wait until you have only a week left. A lot of scams but if you really plan to attend vs. just getting it for the purposes of staying I don't think you will have much of a problem.

Visas are not normal to have perks for duty free imports, although there are some countries with similar for citizenship conversions I recall.

They'd be concerned with some billionaire, or similar, importing a huge estate for basically nothing; then the following outcry from media and citizens.

Thai import taxes are rather steep and VAT is crazy high.

If you are under 50, don't think there is other "good" want to stay long-term however. 50 and over has the retirement visa "also not that great with 800K rotting in a Thai bank", but is still better than 1M paid to the Thai goverment. You avoid all the boarder runs, etc but are still subject to 90 day reports. I'm over 50 so would never consider this option, but also doubt I'd go for the 800K retirement either.

if you go to the Thaipass website it clearly shows you the answer, and yes it is required. If you really want to go, it will be necessary to actually go there and read all the requirements before applying,

you should check out the following forum for latest info

You might be able to get a Covid extension, then get a 30 day extension after that.

under 30 days it's not ever a TM30, but is a different report that they report all foreigners that are staying at the hotel. This is what I used, and it has ALL residents listed, so they just crossed off the other tenants with a pen. Took my hotel all of 2 or 3 minutes to give me the form, and worked just fine.

Education Visa, can register for a 6 month or 1 year Thai language class. However is best to actually go to the classes, Immigration Officers it is easy for them to test you from time to time.