The morning came and while waking up, I made my decision to go with option 2 and simply fly to Yangon.
It was not easy since I wanted to avoid flying as much as possible but taking the overland route would have simply cost too much and lost me 2-3 days in transport.
Getting to the airport in Bangkok by train is the best way if you have some time as it will not only cost you 5 Baht instead of over 200 Baht in a taxi but is also more pleasant and you won't be stuck in traffic.
Stepping into the airport felt strange after suck a long time only taking ground transport, there were checking desks, security checks, enclosed spaces and overpriced shops selling food and souvenirs.
My flight ended up being delayed but at least they had free wifi at the airport so I could catch up on some emails while waiting. I have to thank the two girls who came out of nowhere while I was waiting at the gate, asked if I fly to Yangon, gave me a bundle of Kyat said that Myanmar is great and disappeared again.
Landing at Yangon airport and getting through immigration was a smooth and very quick process. After leaving the baggage claim area, I met the usual taxi touts but here they were different, friendly, not too pushy and while a bit more expensive, still pretty much in line with the standard fare.
Another surprise was just how many ATMs were available and how easy it was to just get some more cash out. Reading online or guide books always makes it seem like there is no way to get money out in Myanmar and you should carry all money you might need with you (advice I didn't follow and just hoped for the best).
The evening was spent having some drinks with a fellow traveler and enjoy the very friendly atmosphere and locals in Yangon. People here reminded me a lot of my first time in Scotland, always helpful and asking if you need anything if you look lost without wanting money or anything in return.
In other words, the first impression was great, despite the ridiculous hotel prices.