1

1. not easily
2. NO...you can go via land China into Laos and then from there into Thailand no problem, but can't go via land from Thailand into Myanmar.
Flying is your best and quickest option...China Eastern fly from Kunming to Mandalay and Yangon.

2

For any backpacker, if you want to travel through Myanmar, you have to obtain a visa beforehand, no VOA, and you have to fly in to either Yangon or Mandalay. (no land border crossing) Unless Kunming has a Myanamar consulate to obtain a visa, probably your best option is to get to Bangkok, then they have same day visa, (full day) and then fly in from Bangkok.

3

Isn't it Myamnar Air that can offer a Myanmar VOA if you fly from Kunming?

4

#2...pretty sure there is a Myanmar consulate in Kunming so the OP should be able get his Myanmar Visa there....no need to first get to Bangkok.

5

Yep, there is a Myanmar Consulate in Kunming, the website advises it takes about a week for a visa. Myanmar Air's website don't advise they offer VOA, in the FAQ they advise going to embassy to obtain Visa. So not real good news for Dave.

6

also note the Embassy is not at the camelia hotel where it used to be but outside of Kumming if staying cloudland ( I recommend great place) they will have info also check at Embassy if Rulli premit driver & guide is open again, overland Rulli to Lashio, you will have to fly from Yangon /Mandalay to Thailand as pemits via tachilek take a while and are expensive and you still have to fly mandalay to Kengtung or Tachile anyway China eastern airlines fly from Kumming and I think Myanmar airlines was from different city
from kumming to Laos take the overnight bus to Oudamsai or Luam Namtha if you are heading to Thailand via Houyxai/ Changkong border and not travelling down through Laos, which you should if at all possible dont get bus just to border Boten or else you will be ripped off by the minivans to Luam Namtha