Hi Kerry, you can stay till 27th July. Then you can do a visarun to Penang to get new Non Immigrant B visa. Just be adviced that, when people use their visa more than 12 months, Penang Consulate check how many months of remaining validity your work permit have, it must have at least 8 months of validity. In your case, work permit renewed in April, new visa applied next July, it should be ok. Feel free to send me message if you need more info.

Do you live in Phangan or Samui?

They ask to show 20,000 in cash at border if you cross by land at Sadao. Penang Consulate doesn't require financial proof for SETV. It does for Ed Visa.

Correct Tod, Penang requires return ticket and hotel booking or house rental contract.