Ad 2:
@John *********
, you always can do a border hop/bounce to Cambodia, Laos or so, and come back for a exempt entry of 30 days (From 1st october probably 45 days), and extend it again with 30 days. You can do this only 2 times by land border. Or go for a visa run, which is buy a visa again in a Thai Embassy or consulate in the mentioned countries. But a bit more stress these border hops/bounces/runs. Also depends how far you are from a border. Otherwise you have to fly in 🤷♂️
Good luck !!