Tipping for luggage handling?

[TheDuckRocks]

We are going to WDW for the week before our cruise and will be using DME to get from the airport to the resort. We have purchased transfers from the resort to the port and to the airport as part of our cruise package.
We are used to tipping bell services when we use them as well as SkyCaps at the airport, paying $1 or $2 per piece of luggage.
Can I call for bell sevices to pick up our luggage on the morning we leave for the port and will they get it to the bus? Or does it travel separately?
When we get to the terminal do we have to reclaim our luggage before boarding the ship?
Is there someone we tip when they deliver the luggage to our stateroom?
On the return how is the luggage handled before leaving for the airport? And how does it get to the airport? And do we reclaim it before it goes to a SkyCap if it goes to a SkyCap?
How many times should I be prepared to tip?
Boy, I guess you can tell I've never cruised before. Thanks for any info you can share with me.

[ElenitaB]

Kay, you're a woman after my own heart. I also tip everyone who helps us in our travels. Here's some answers to your questions:

• Can I call for bell sevices to pick up our luggage on the morning we leave for the port and will they get it to the bus? Or does it travel separately?
  I was under the impression that DCL would contact us regarding our luggage. However, they never did so I called. A porter came by early the morning of our cruise to pick up our luggage and yes, I tipped him. Your luggage travels separately from you. If you wish to have what you're taking with you put in the bus' luggage bay, your driver will be glad to do that for you.
• When we get to the terminal do we have to reclaim our luggage before boarding the ship? Is there someone we tip when they deliver the luggage to our stateroom?
  You don't reclaim your luggage; it will be at your room when they drop the ropes to the cabin areas. Also, I really didn't need our rolling carry-on and was able to leave it in a special area once we got off the bus and it was also at our room. You more than likely will not see the person bringing your luggage to your stateroom.
• On the return how is the luggage handled before leaving for the airport? And how does it get to the airport? And do we reclaim it before it goes to a SkyCap if it goes to a SkyCap?
  We didn't return to the airport but went back to WDW. Some of the experience is shared, however. You may leave your luggage outside your cabin by 10:00 or 11:00 the night before you debark. It will be picked up and you won't see it again until you get off the ship. We enlisted the help of a skycap at port and it was the best decision! He found our luggage and had us through Customs very quickly. You can also chose to bring all your luggage off the ship with you (but I wouldn't recommend it). Your carry-ons you do keep with you (some people have reported packing away their clothes for debarkation day, but you wouldn't do that! )
• How many times should I be prepared to tip?
  I made a spreadsheet for our gratuities (in case you wonder, I work at an accounting firm). It included: skycap at home airport, DME driver, resort luggage porter, DCL driver to port, stateroom host, server, asst server, dining room head server, spa CMs, singles for room service, skycap at port, DCL driver to resort, CM at our resort who unloaded luggage from bus, DME driver back to MCO. Yes, it is a long list, but it's what I expect to tip when on vacation! The spreadsheet helped me determine how many bills I needed (i.e., how many singles, 5's, 10's, etc.); I also had the envelopes prepared before we left.

[TheDuckRocks]

Ellen, thank you for the help.
You got me laughing as the reason I posted these questions was because I had been working on my "WDW Budget" spreadsheet when I ran into a wall trying to figure out the tipping thing. BTW before I retired I worked in accounting and will use any excuse to make a spreadsheet. Sad.

[ElenitaB]