I want to start with something simple to warm up. This fits within my comfort level quite well because I have built many comparison sites before, for example:
This gives me the flexibility to create my own content types like 'Ad Blocker' which could consist of: Title, Description, Link, Operating System, Browser, Price, License, etc (That's my list of fields so far, but CCK allows me to change any time).
Views should let me display/sort the data any way I want.
I think standard grid should be fine, I may use Contemplate if I have to stylize the output for any reason.
Other Modules I will probably use: token, pathauto, disqus, more later.
The obvious two are ads and affiliates. Generally, it's a high paying niche for spyware/anti virus type stuff.
Some google keyword bids (exact match):
Ad Blocking $1.71 ad blocker $4.28 ad blocking software $6.77 pop up blocker $6.26
I am familiar with some options (I use Ad Block Plus), but I am sure there are many out there.
I think that about sums up my thoughts right now, I will build it and see what changes.