You've obviously already done some very good research. You're asking a lot of very good questions.
In many ways, buying a condo to be a rental unit is no different than buying a detached, single family home.
Add up the costs - all of them, including maintenance, property management, HOA, a set-aside for long-term maintenance, a cushion for miscellaneous, as well as the monthly mortgage, and see where you are. Will you be able to rent the unit for more than it's going to cost?
If the answer is yes, even by only a small margin, then you've passed the first test. Once you add in the tax advantages of owning rental property, you should be in very good shape.
Sometimes though, even if the calculation leaves you upside down a bit, you might be ok after taxes.
I once read (I apologize that I don't remember who to give credit to for this...) that a good rule of thumb is if you can buy a rental property that will rent for 1% of the purchase price, it's almost impossible to lose money. In other words, if you pay $100,000 and can rent it for $1000 per month - you're good to go. Until about two years ago, this equation didn't work anywhere in Denver and nothing was even close. As recently as about 18 months ago though, I saw many properties where it did work, so we're at an interesting time to be buying.
As for the HOA costs specifically, you're probably right, in general. I'm not sure there's a 'plan' for them to rise and rise as you describe, but that's probably the reality. It takes each development a little while to really understand their true costs as the property transitions from developer to HOA-direct managent. Also, different HOA's have different philosophies in terms of things like how much they want to set aside for long-term maintenance - new boilers and roofs, and pools, etc. Very conservative HOA's set aside much more for these things, and that's reflected in the monthly cost, but the advantage is that 'special assessments' are much less likely.
So - in my opinion, the best plan for you would be to find a bank-owned unit in a well-managed, existing development at least 3 to 5 years old, which has very little history of such units. Or maybe a unit which is quite a bit older that you can update a lot. Updating a condo - top to bottom - is much less expensive than doing the same on a house, so the return can be higher. This should allow you to buy low, hold, and sell for maximum return on investment, but all the while having very predictable costs.