Getting organized, Packing, Airplane Carry On Baggage - Can be costly!

The countdown is on and I have a little more than a month before I have to move out of my wonderful condo in Toronto.  So far, I've managed to get my things organized in a manner that has allowed me to assess what I can bring to Japan.

Keep in mind that I will be travelling to Japan with a stop over in Hong Kong.  Because I am technically travelling on two different flights, I will be charged for each leg.  I booked my tickets through United Airlines, using the lovely Google Flights tool to find the cheapest ticket.  United Airlines gives you the first check in baggage at no cost.  But they really get you on the second check in.  From Ottawa (where I'm leaving from) to Hong Kong, they charge $100USD for one baggage.  From Hong Kong to Japan is an additional $75!

All in all we're looking at about $200 Canadian to lug a bag full of clothes from Canada to Japan.

So the obvious question is, is it worth it?  Is the value of my baggage equivalent to the cost that I incur by bringing it with me?

In short: I don't know.  But I've decided to bring that second carry on anyways. So I will be bringing with me one large backpack,  one large suitcase, and a carry on backpack.

I picked up a 28" Swiss Gear expandable shell case on sale for about $140 after taxes at Sears a couple weeks ago and I think it should be suitable enough for what I'd like to pack.  Keeping water proof and protection in my mind, this was the only one that fell within my budget.  So far my "important" things to pack are:

-  Computer stuff:  External Hard drive, keyboard

-  Dress Shoes, one pair of sneakers

-  Suit, ties, dress shirts, dress pants

-  A couple books

Keep in mind that I only have up to 50lbs per check in item.  So this will be very challenging.

I figure that my bag of clothes will likely not exceed the limit, so if I go over on my suitcase I will just do some shuffling at the airport.

I also just recently picked up a small carry on backpack that can carry my laptop, ipad, and other essentials that I would like to keep by my side.  I've always used pretty cheap backpacks in the past, so I decided that I would pay an extra few bucks to have something that will last me.  So I decided to pick up a Swiss Gear 17.3" Laptop Bag from Costco:  Swiss Gear Backpack.  This bag is perfect for me considering it has all types of practical applications in the bag: key holder, cell phone holder, laptop strap, Ipad slot, etc.  In addition, the quality and make of the bag is pretty good I must say.

Thought I should include that it was just a coincidence that I ended up with two Swiss Gear products.  In no way do I have any affiliation with the company!  Given my budget and product expectations,  Swiss Gear just happened to be the best fit.

Keep you posted!