Look at the price point of the various kegs you're looking at. Generally, there is little to no cost savings at the smaller sizes. In fact, a new 5 gallon keg often goes for the same price as a new 2.5 gallon one. You're not saving much by going to the smaller size, and you'll be kicking yourself the one time you need a 2.5 gallon keg and only have a 1.75 free. The only reason I'd want the smaller keg is if I was under space constraints and that was the only size that would fit.
As a matter of fact, if you're planning on fermenting in them, then I'd just spring for a 5-gallon right now so that you could move up to 3 gallon batches at any time if you ever felt like it.
If you're looking to pull the trigger right now, I think Austin Homebrew Supply has the best deal currently. New 2.5 and 5-gallon kegs are $79.99, which is the same as when AiH goes on sale. They also have a free shipping promotion for orders over $50. Kegs are excluded, but you can do what I just did and buy your kegs on one order, then place a second order for all your supplies - taps, hoses, disconnects, spunding valve, etc.
I'd also recommend one of the small portable CO2 chargers that runs off the 16g CO2 cartridges. One of the big advantages of small kegs is that they are easily portable. The mini chargers are great for bringing a keg to a party, tailgating, etc.