Visitor Visa and my flight home dates.... confused

Lot of questions… so Thank you in advance for reading this thread.

Background information:
I have a 60 day multi Visitor Visa.

It is to my understanding that I MUST have a flight home purchased or currently have possession of a booked flight when I renew my visa.

Well my flight HOME to the USA, is in 5 days… and my Visitor Visa doesnt need to be renewed ( for the first time) for another 28 days.

Do I pay the penalty of $400 and change my flight?
Or do I let it run out… and buy a flight to Hong Kong when I need to renew my visa?

Misc. Information:
I do not have ARC… I have not been able to find work here… I keep getting the run around from English teaching schools.
None, ever call me back after filing out applications.
So I am concerned that if this goes belly up and I need to go home… its going to be crazy expensive to fly home.

Maybe I can change my flight multiple times? for each 60 day time frame?

Im a total noob to this. I do have a support system here… my girlfriend… but money is getting tight… and its getting stressful a bit. Though WORK from home is keeping my spirits up… Im not flat broke.

Hey Andrew,

Just want to ask what part of Taiwan are you in? Taipei?

When you talk about the $400 dollar penalty to change your flight is that USD or NT? If it’s NT just go ahead and change it, if it’s $400USD then you need to decide if you want to continue the job search here or go home and pursue other options. Since you still have a month left on your visa why not try to get your money back for that flight back home and wait to see how things turn out. I’m not sure about ticket prices but I think a roundtrip ticket to Hong Kong will run you about 12,000NT bought without much notice. Again I’m not sure look into prices yourself. With a month left on your visa you can find a job, even as a newbie if you are flexible and they can work out everything so you don’t need to do a visa run. Here is what I’d do to find a job if I were you. - look at teaching jobs and blitz all the recently posted ads in your area.
facebook - need a sub teacher or want a sub teacher in Taiwan group(plenty of new jobs ads and sub jobs to help you make ends meet!)
dewey - google dewey taiwan and scan the ad posts
asian consultants international - scan the jobs there

If you are willing to move you can get set up in Taoyuan, Hsinchu, or Taichung pretty quickly. I’ve seen many ads desperate for teachers and willing to hire newbies. If you’re in Taipei look into subbing while you search for full time work. You have to make some phone calls and send emails like crazy but you’ll find something pretty easily.

Thank you very much for your insightful suggestions!

If I’m not mistaken, with a multiple entry visa you can extend your stay twice, up to 180 days in total. But you must have a valid reason to show.

There is supposed to be a boom for english teachers here because of new public education requirements. but i’m sure you already know that…

what new public education requirements?