Jimmy - you've hit the nail on the head - Cabo has just gotten to be not for the faint of heart price-wise. Thus the full disclosure for Jamie.
I concur re hotels. Now this might sound weird and of course our place doesn't compare to Las Ventanas, but it's about 1/3 the price, so it shouldn't.
My wife and I have stayed three times at the Presidente Intercontinental, in San Jose del Cabo. It is an all-inclusive resort, meaning one price for lodging, food, drinks.
I turned up my nose at it the first time, figuring it would be nothing but burgers and beer and while that's fine most of the time for me, on vacation I've come to want more. My sister and her husband made us go.
We've come to LOVE IT. Five restaurants there, only one of which is buffet style. Very relaxed, very fun, very high-quality. Rooms are not absolutely first-class, but they are very nice. And one can get very good deals, as I mention.
This also brings up a key point about Cabo - the town of Cabo San Lucas is VERY fun, but understand it is a complete tourist trap and spring-break capital. That is, it's wild in a drunken collegiate kind of way. My wife and I having left that behind - sadly - a few years ago, we no longer bother even going to the town. But yes, if you are into the wild partying, then Cabo Wabo is great, as is Squid Roe and the Giggling Marlin and several others. You are guaranteed to have wild "collegiate" fun at any.
We've also found though the the town of San Jose del Cabo - on the airport end of the corridor - is very nice - it's a small, sleepy, authentic Mexican town, with some very cool hole in t he wall type restaurants. Although we've become loathe to leave the "campus" of the all-inclusive resort, we always do a walking tour of San Jose del Cabo and always do find a new little restaurant for lunch. It's very cool.
One other key point: Jamie seems to want on-site golf, and that is few and far between... damn near all courses you'd have to take a cab to, or a hotel shuttle. That's no big deal - just don't expect to roll out of bed and walk to a range. That CAN be done - particularly if you stay at "The One and Only Palmilla" or any of a couple resorts attached to Cabo Real - but it is the exception and not the rule. Golf is primarily a taking a cab to it affair.
BTW, this last trip I played the 9-hole course at San Jose del Cabo - now called Mayan Palace GC - and it was VERY fun! No scenic beauty - surrounded by condos some in half-built state - but great golf, very strategic and very fun. It's also the closest thing remaining to a reasonable price.
Many other courses are in the building stage - there's an article in the current Links magazine detailing those, and other great Cabo info. Just understand that if you did the trip the writer of that article did, you'd be in for five figures.