Is that even possible ?

My friend (seriously, I do have one) normally gets a double-entry Tourist visa each winter, does the Extension, then the border run and then another Extension which is usually enough to get him through the worst of a Canadian winter. Generally stays 5 1/2-6 months each year.

But recenty Thailand started using the "e-visa" online system. Last year he tried it and after a dozen failed tries gave up and just got a (45 day) stamp on arrival.

He tried again this year and the same problem. It told him his password was no good. They sent him a temp password. It didn't work. He tried again. Same thing. After half a dozen tries he gave up. (He's getting into his upper 70's and computers are not his friend.)

He is hoping he can arrive on a (30 day) stamp and convert that to a (double-entry if possible) Tourist Visa.

I looked at both the TM.86 and TM.87 forms and they are identical except for the title. One is an "Application For Visa" (TM.87) and the other is an Application For Change Visa" (TM.86).
(I downloaded them both and have them open in different windows right now.)

Everything else on the forms is identical and it's the same fee for both (2,000 baht - mispelled as "BATH" on the TM.86).

Because some barstool know-it-all fed him a story once about how all banks rip off the accounts of all foreigners in Thailand, he's not too keen on keeping a large wad of cash in a bank here. And at his age, well, even if he did leave a large sum in a Fixed Term Account (as I've told him would be just fine) - he's worried he may croak in the arms of some young (40ish) honey and his money would be lost.

I've tried to get him to go the Non-O route and showed him how cheap and easy it is, with the advantage of being able to stay as long as he wants or return earlier or whatever, but now of course you have to leave 400k in the account all year (or, like some of us, leave it all in there all year anyways). Again though, if he croaks (here or back home) his money would pretty much be lost. (Even with a Will, it would be hard for someone back home to come here to claim the money.)

He was thinking of just going to an agent to get it done but as most of you probably know, they'll charge him 10 times (or more) what it would cost him to do himself. (He has no problem going to Jomtien to do Extensions all the time so doing this himself would be easy.)

Of course, the other option is the Non-0 but - from what I can find, unless you get a (rarely issued) multi-entry Non-0, the best you can do is get the 90 day initial stay and then extend it for a year ? 
Would they extend it by just 2 (or 3) months if that was all my friend wanted ?

Once buddy gets here I can sit down on his computer and try to sort out his online application issues but that probably won't help him this year.

(Unless he applies for the e-Visa after he arrives here, gets the electronic approval, does a border run and then uses the e-Visa to re-enter Thailand ?)

That or arrive with the 30 day stamp, extend it, then do a border run, then another extension, then another border run. Sheesh - it would be cheaper to pay an agent !
 

Not possible.

All he can do is get a 30 day extension.

Or a Non Imm O Visa followed by a 12 month extension for retirement if he has 800,000 in a Thai bank.