I am going to be going there on May 5, I pretty much have the everything planned already. The boards a usually free in the airline depending who you use, I would call the airline and check to make sure of that (Delta, continental, frontier, are all free). Snowolf posted answered a lot of my questions in this thread http://www.snowboardingforum.com/sno...-question.html
he is a really cool guy.
Hotels near Timberline the only resort open at your time, tend to be expensive. I am staying at "the resort at the mountain" Mt. Hood Oregon Resorts - Resort at the Mountain - Mount Hood Lodging
for about $350 total for 3 nights. I found some cheaper motels and cabins closer but I am not sure I want to stay at the motel Welcome to the Snowline Motel!
, and the cabins are to expensive for 2 people, but for 5 it should be perfect with lots of room you can find that information in here Villages of Mt. Hood | Monthly Web Magazine
go to the timberline website Timberline Lodge - Conditions
and check the conditions they are amazing currently 236" base and 732" snowfall to date, that is insane. You picked the right year to go summer ridding, right now timberline has a spring pass for $99, maybe they will do something similar with the summer pass.
With the rental car this is the way I do it, car agencies prices vary very fast. Just make a reservation the cheapest one you can find for a comfortable car for 5 people (SUV or minivan, i guess). Then check like every 3 days to see if the price goes down, you will be surprized at how fast they go down and up. If you find something cheaper cancel the previous reservation and make a new one, remember you only need your name and email to make a reservation, no credit card. The easiest place to search for the best car deal is Orbitz: Cheap Travel, Flights, Hotels, Vacations, Car Rentals, Cruise, Activities
And for airlines I search with hotels
but I buy the ticket directly with the airline after I have selected the best flight for me.
I am sure Snowolf will add to this post, but just felt like sharing what I knew about the place.
Good luck with your trip.
If you have any question let me know, I will be more than glad to help you out.