I can't remember when I paid for software. There is just so much freeware available to do every task you can possibly imagine that it's not necessary to pay for it. One exception to the rule is Windows. Although I don't pay for it directly, I know it's included in the price of my laptop.
Of course, I mean its free right? The only problem with these free software's is that they include, sometimes, ad-wares and other software's during the installation, that's why you should really read what's flashed in your screen rather than just hitting 'I accept' every time. When downloading software's for free, specially from Download.com, you have to be careful and read everything. Another good way to avoid being inconvenienced by these free stuff is to install a good antivirus and anti malware software in your computer, I recommend Ad-aware and Malwarebytes, both of them are free to download.
It is not certain that if you download a software online it will come with viruses. In most cases you just need to find the appropriate website to download your softwares. I think if you just download your software from popular and safe sites there is nothing to be worried about.
Yes, i honestly do it download software online. I mean, it's just too tempting not to. There are literally thousands of available free software online so why not download it? I don't feel guilty or anything. People do it all the time. I think that's the downside of the technology nowadays so we might as well benefit from it. Of course, i have to be sure it's safe to download first before i actually download it. Some are just viruses, so it does help if you have a good antivirus.