What Would Warriors Do? Site Architecture Advice Needed

Hi everyone!

Long time lurker, first time poster here!

First I'd like to say that I'm blown away by the wealth of information provided by this forum. Thank you to all who take the time to contribute and help out newbies like me. I hope one day I'll be able to pay if forward!

My Idea:
I'm looking to start a Travel Planning & Tips/Couponing & Deals site (or blog) for a specific destination. I'm not trying to compete with the big boys, I'm just looking to create an awesome resource for travelers on a budget.

I realize this might not work, and I have a long hard road ahead of me, but I believe in my idea and really want to give it a shot.

MY PROBLEM:
I have NO CLUE how best to approach setting up the structure of this site.
I'm TOTALLY confused by the whole posts & categories vs. Pages & child pages.

And don't even get me started on siloing! I understand the idea of silos, I just have no idea how to make it work in this situation or if it's even advisable.

Another area of confusion for me is this. Hotels, restaurants, and attractions, have general information and then they have coupons, deals and discounts. Should I combine the information and deals onto one page or break it up into two? (Silo confusion rearing it's ugly head)

What would YOU do for a site like this? A site that has a lot of "evergreen" content, but also a lot of "news/time sensitive" information (ie: deals, special events, coupons).

So, if anyone can decode the complete and utter non-sense I've just written, any help would be GREATLY appreciated.

And if anyone knows of a reasonably priced service that would be beneficial for me, I'm all ears!

Thanks!

Andrea