Assuming you mean Visa On Arrival for LAOS. You just do this at the border as you enter Laos. Can't recall the cost, but it's not expensive. An agent can't physically enter Laos on your behalf. It has to be you. I know some people believe agents can do anything, but reality is somewhat different!

Canadians must use the income affidavit method to illustrate monthly income. As

@Brandon ***********

has indicated above, it all depends whether your embassy would be willing to verify that you have a minimum monthly income of 65,000 baht. They have no problem doing this for the fixed pensions (I have a Canadian neighbour who I assist with his annual extensions). Check with your embassy and please do report back here on the outcome as this may assist others.

@Ronald ********

60 day entry is tourist visa, not visa exempt. You get only 30 days (45 from October 1)

@Ken *******

If he's on overstay, he's on overstay. A friggin dentist can't sort it out! 🤣🤣🤣

@Bonnie ******

I think the OP is talking about settling in Thailand, not travelling through other countries and taking cruises!

@Bonnie ******

Perhaps you should explain the strategy?

@Christina ***

He's from the US, not eligible for VOA. He can enter without a visa, but can't keep flying in and out every couple of months. Eventually he'll be denied entry

Get a 10 year Elite Visa. Easiest way to put in ten years. Get a one year extension on that, and then you'll be eligible for a retirement visa.

@Will **********

He doesn't need 20 years. In 10 years he'll be close to getting a retirement visa. So a 10 year Elite will suit him fine

Official government infographic