@Tod ********
awesome thank you so much! I'll just give an update as to what we experienced through the SADAO land border.
My friend is Thai and has their own vehicle, and got all the vehicle stuff (Malaysia license plate sticker, etc) sorted before going. We forgot to get vehicle insurance for Malaysia, but it is offered near the border station (1000 baht per month). You can also get money exchanged and a Malaysian SIM, but I purchased 7 day international roaming for AIS - 99 baht for 2gb. We filled out the paperwork at immigration at about 8am and there was no line. Charged 25 baht for the driver and 5 baht for each passenger. No issues and took about 20 minutes to go into malaysia. We came back through 4 days later at 10pm. I had no issues at immigration (previously spending 60+30 days in Thailand). It took about 20 minutes to come back through, and there was no line. 25 baht for driver and 5 baht per passenger again. It was much easier than I thought, but it was also more paperwork than coming by air. They gave me 45 more days in Thailand.
Gas in Malaysia is only about 16 baht/litre!