@Nikola ***********
It's not too bad at all. It's just the Bokeo-Boten section, which can be covered in as little as 3.5-4 hours by minivan or private transfer, that needs to be done by road but once you're in Boten, the train is super fast and whisks you down to Luang Prabang in no time. It takes about 2 hours. Then it's 1 hour from there to Vang Vieng or as little as 1h50m to Vientiane from Luang Prabang, if you're on the express service.
If you fly from Chiang Mai to Luang Prabang, you might be obligated to purchase an outbound ticket from Laos as one way tickets are usually frowned upon by airlines. Lao Airlines flies this route and I was reading Bangkok Airways does too (but check again, as Bangkok Airways is notorious for starting services then quietly ending them just months later). The airline might still let you fly on a one way ticket, but generally, it's a lot less flexible than if you go by land.
You could also do the slow boat from Huay Xai (Bokeo, Thai border) to Luang Prabang and thus avoid the roads.
Almost everyone uses the train instead of the roads on the north-south journey, unless they come by car or like adventure. If you enjoy adventure, then you'll have no problem with the highway trip from the Thai to the Chinese border, where you catch the train. The road trip from Luang Prabang to Vang Vieng is much more nausea inducing and often takes longer as well.