You will not be able to get a new long-term visa or extension from immigration (for example a new work extension) until you cancel the previous one. You would then receive the fine of 500 baht per day (to a maximum of 20,000 baht) for failing to cancel. Immigration doesn't care why you didn't do it, they just know that you did not as you agreed to.
stop giving bad information. We're not talking about overstay. We're talking about an education extension. You won't be fined at the airport. You'll be fined when you go to immigration in the future when they see you failed to meet the requirements of your extension. And an extension is not the same thing as a visa. We're talking about specific extensions here.
that will invalidate it if no re-entry permit was purchased. But that doesn't mean it was cancelled properly and is a failure to meet the requirements that were signed when getting the extension.
Work extension, volunteer extension, education extension all have a provision that you must notify immigration if the basis of your extension changes. This means even if you just let it expire, you are in breach of the documents you signed that said you would let immigration know of any change in status. All of those extensions must be cancelled with paperwork from the sponsor or else you can be fined 500 baht per day for failing to abide by the agreement you signed (up to a maximum of 20,000 baht) and can also prevent you from getting a different long-term visa or extension if immigration or the embassy notice that you failed to cancel the previous extension.
Most embassies will not process a visa application if you say you'll be traveling more than 3 months away. So pick a date between 6 weeks from now and 3 months from now.
And DTV does not give you 5 years in Thailand. You get a 180 day stamp when you arrive. So your exit date should be within 180 days of your arrival date.