Work/visa question

I’ve been in TW for 2.5 years. From September 2004 to April 2005 I was without an ARC (student visa and 1 60 day single entry visa). As well earlier I had overstayed and I can’t get in visa-free until this July. Right now I’m in my hometown in Canada because the HK visa office only gave me a 14-day visa. I have, as I see it, two choices if I wanna get back into TW: (1) come in on a landing visa (30 days) and make a visa to KL or somewhere to get a resident visa or (2) try to get a 60-day multi-entry visa in Vancouver (given the extreme shortness of the visa I got in HK, that may or may not be a problem). Which do you think would be better?

Thanks in advance