Transformers do not need to match in wattage.
You will need a minimum of 3 transformers - one for the main loop and one each for the ascent and descent grades. You may need feeder wires on the main loop to even out the voltage on the far side.
Used transformers from a reputable source are a good deal, especially the big postwar units like the KW (2 separate throttles for 2 trains) and the ZW (4 separate throttles for 4 trains).
Here is a tutorial in phasing transformers.
As your railroad grows and you add multiple transformers, it is important to make sure that they are all in phase. All that this means is that the common and hot terminals of the transformers are...
Hope this helps.
Enjoy your trains!
Larry