Pity the search function has been deleted, or I could probably have found the answers already.

 

Anyway.

If I can't get my extension as I had planned, I need 3 months from expiry of present extension before heading to the UK on business for 2 or 3 months. I would go to Penang for a tourist visa which would cover that.

Then I would apply for another tourist visa in London to return to LOS, or is that too soon under the new rules?

After that I would go to Penang for another Tourist Visa, but would that be allowed?

If not, I'd have to fly back to get a visa exempt at the airport, but would I be allowed to enter if I had just been on a tourist visa?

It's all getting very complicated now.

No, yes, yes to your three questions.

A return to the UK for two or three months should ensure immigration leaves you alone for a while. It is one of the best ways of convincing them that you are not an illegal worker, and still have ties with home.

There is no limit on entries on Tourist Visas - you could leave, get one, and come right back.  You do, however, need to be able to show 20K in Cash or Travelers Checks, and say exactly where you will stay in Thailand and explain how you can afford to be here.  If gone for a couple months and returning, they are less likely to request these, but if you visit frequently and/or stay for extended periods, that chance of questions goes up - especially at Airports.  Be Prepared so you can relax and not worry about it.

 

Entering Visa-Exempt is another thing entirely - repeated entries on Visa-Exempts can get you questioned, warned, and even denied-entry.

 

As far as getting additional Tourist-Visas locally after you return:  Every consulate has its own rules for how many you can get in a single passport and/or whether "time away" has any effect.  Generally, you can get 2 to 4 TR Visas from a single consulate before being denied another or getting a stamp added to your visa which causes you to be denied any more after that one at that consulate (and some other consulates) in the future.  The solution to this is to rotate consulates and then periodically obtain a new passport.

Thank you for the replies.

Hopefully I'll get the extension, but at least plan B would seem to be viable.

I'm getting too old for all this though, so hopefully I will get a last hurrah and even get to go back to my old beach favorites, before I have to hang up my travelling hat.