This is shareware, so there are some things we know.
There are people who want to use your software and are willing to pay for it. All you have to do for them is get them to try out your software and not make it difficult to pay. (For me, Paypal is quick and easy, but sending out a check becomes a hassle.)
There are people who simply do not pay for your software, and what they do does not affect you. Perhaps you are a little better if they are cheating; That way, they might be of interest to someone who could pay you. Try stopping them from using your software if you want, but don't force yourself to think that it will give you more.
There are people who are willing to pay you, but prefer to use it for free. These people are the ones you want to worry about. You want to do it less to just pay you than to cheat. If the cost is reasonable, they are not going to invest unreasonable amounts in its use, so you do not need to take excessively restrictive measures. (Remember that only people who will work are hard to fool those who will not pay you anyway.)
Remember also that protection from excessive irritation will cause people to “pay” for “not pay.” Many modern examples, by contrast, I really don't think that annoying your legitimate customers is an important part of a business plan.
Here you can’t do anything without waiting at home to cause many other problems, to prevent everyone from cracking your protection scheme, so if it’s worth it to sell in the first place, someone will crack it and probably put on a pirate bay. Do not worry about it, as you can do nothing about it. Save your efforts for things that will bring you more profit. EDIT: Be very careful in protecting your application. You do not want the Pirate Bay version clearly superior to the legal version. You also want legitimate customers to say, “It's great, and not a problem to install,” not “He turned off my DVD drive and soaked my gerbil, but after that it was great to have.”
Finally, I do not see the difference between Windows and MacOSX here. If I download some shareware files for Windows, I save the ZIP file and I can delete and reinstall, or reset the system date. For MacOS, I can remove and reinstall, or reset the system date, and Time Machine can automate some of them. What is the problem here? (Remember that if you leave unused bits where they can cause problems later, you are potentially annoying cash customers.)
My recommendation would be to not worry too much about it.