I think doing everything in 30 days is a bit much, as you may also need to wait about 15 workdays for the visa. No worries, enough options to stay longer.
After you get married and get the Non O spousal, you do not need a retirement visa or medical insurance.
Also get your future wife to help you out what to get and where to go. Together you can do everything, alone you may find it difficult to communicate what is required, and she also needs papers for marriage.
I have to disagree on this. I came in on a tourist visa, and changed to a Non O spouse visa in Mae Sai. I was advised to do it this way, and it worked out fine.
I believe normal phone companies are not the best or cheapest way to communicate.
With good internet, which is all around, Messenger and Whatsapp are fine. I use Skype also to make a few calls. I am not sure if Messenger and Whatsapp can call landlines, that is why I use Skype. Very cheap, I am too lazy to look for an alternative.