after the 1st year it will. But you need to maintain required balance and not let it drop below. You can use the funds but it must be back up a few months before applying for extension. You can use an agent to 'make the funds appear' but that is another discussion. Brandon is very knowledgeable, definitely take his advice.
Enjoy. Don't drink and ride. If you don't know how to ride a motorbike, don't start learning here. Shoes off in people's homes. Respect goes a long way. People are much kinder and genuine than the states. MUCH BETTER and healthier food. Try everything.
Very possible but more running around, cost. My recent experience, I had to get thai license, immigration paperwork, purchase 1 years insurance to open bank account on tourist visa and apply for non o based on retirement. It's definitely easier to do if you apply from you home country then apply for 1 year extension once here.