Is it possible to apply for a Tourist Visa after exiting Thailand to stay until mid-October 2019?

Trying to evaluate a Plan B

To the Oracles of this splendid group.

My OA Long Stay is expiring 6 August 2019

I will have had 2 years out of it by then.

I have a Lease on a condo expiring mid October 2019.

Original plan A was to return to Australia August 6 and apply for a new OA long stay. Then assuming it was approved make my back to LOS for another 2 years.

Fly in the ointment

Possible Health Insurance requirement. read it again..

Possible!

I'm 73 years young but cannot get cover that I can afford....if indeed the Health Insurance is made mandatory.

So Plan A goes in the bin. NO return to LOS.

So plan B is I exit LOS as required on 6 August 2019 ...but go to say Penang or another close city and apply for a Tourist Visa and if issued come back to LOS see my Lease out by mid October 2019 and return to Australia at that point.

Is this doable?

I'm in Pattaya so which exit to which country for a tourist visa would be the most sensible?

I'd be coming back into LOS for approximately 2 months.

Please advise.

And whilst a little off topic...if the Health Insurance becomes law for OA Long Stays I expect there will be one or two others facing same predicament...Has anyone an opinion on another Asian Country?