I don’t have a lot to add about lifestyle especially after golfgal’s excellent post. I will focus on numbers here.

I suspect that you will find that there are some phenomenal deals right now. Especially if you can limit your monthly outlays by buying something with a lower HOA. Much of the driving force behind the rise in HOA’s is the delinquency rate among the owners in the building. This has a self-limiting effect. See below:

I am aware of one group of investors who stopped paying on about 22 units in Acqua Vista (425 WBeech), La Vita (300 W. Beech), and 350 West Ash (you can probably figure out the address for that project). One agent listed all of them in the space of a week. This group was trying to sell as they went default. I submitted several offers for buyers. When I called the agent to get status on the offers he informed me that he had canceled the listings because the sellers had stopped returning his calls. Now all of those units are likely going to go bank-owned. They will resell for dramatically less than the previous owner paid. That sucks for people trying to sell but is good for the other owners. The hoa dues will likely be easy to pay for the new buyers and they will be less likely to default after purchase.
We are finding the bottom in some places right now. In Acqua Vista the 2-bedroom bank-owned places under 300K are leaving the market right now in droves. Often they are going to contract with 10 offers and a bidding war. I have just counseled clients through their 8th rejected offer in that building. This bottom boom (insert beavis-style joke here) is facilitated by the fact that this building is in a giant default meltdown. It may go lower in that particular building but I doubt it will get a lot lower. Almost every place closing escrow has cash or high down offers. Additionally as those units re-sell, while its unlikely that HOA dues will come down, they will likely not go up for years once they stabilize.
Another complex to keep an eye on is Piazza Palermo (1501 front). Comparatively lower dues and similar (or better) amenities. Fewer defaults but better deals.