Hua Hin is probably the best immigration office in Thailand. Always polite and usually not a long wait. I really appreciate the help and fast service there!
On appointments: if yours is a long way out check back daily as cancellstions are frequent and you might be able to pick up the cancelled time slot if you check at the right time?
Just a bit of experience. Watch a few of the YouTube videos by former usa visa officers. Some have some very good advise such as: Most people go in with a load of documents and wait for the officer to ask questions? That seldom works! The default opinion is that you will overstay. He will ask a simple question or two and probably hand you a denial form. What you have to do is after the first question start talking and explain what you are going to do, why you must return to Thailand and what your ties to Thailand are? Family, business, real estate owned, job etc. He will have a few dozen applicants after you to see today and you have about 3 minutes to convince him that you deserve a visa! Take your paperwork just in case he wants to see something but it's unlikely he has time to look at anything? And no he probably has not had time to do much if any prior research as to your papers before today? Best of luck!
I don't think so because the reentry office is just after the immigration checkout point? But possible? You might consider just getting a multiple reentry permit for 3800 baht.
The office is just past immigration. To save time print out the form before going to the airport. I have used these at both airports. However now I get the reentry permits in advance because if for some reason you can't at the airport your visa or permit to stay will be canceled and you have to start over when you return. Too stressful at last minute!
If you do an OA you will need to buy health insurance.
Come in on visa exempt.
With at least 15 days left go to immigration and convert to a non O. Open bank acct and deposit 800k baht. Go back to immigration at the time they tell you and extend the non O for one year due to retirement. While at immigration get a certificate of residence as you will need to open bank acct.