The command line program, wget, can do most of what you want, but being a command line tool there's a slight learning curve.
Googling for alternatives with a GUI I found visualwget but I can't personally vouch for it (or its safety of the executable on Github) as I've never used it personally.
For Slashdot you can fetch the page for a particular day with a url in the format:
Where in this example the ?issue= is followed by a date in the format YYYYMMDD and using this I was able to go back to the beginning of 2000.
You can further filter it to a topic, in this example to the topic technology, by using the ...
WFDownloader App can download images while crawling a website. It also meets your other criteria like being free and being able to run on Windows. You use its crawler mode to achieve this.
Open the application and go to Tasks > Add a batch download via manual links fetcher.
Enter the URL you want to start the search from, select "Crawler mode" ...