Sorry, but that's not how that works. There's no guarantee that we'll get $250K for anything. The real worst case is our trademarks expire, we fail to renew at all, and a company (like MS) comes along claiming they own the mark and/or want the domain, demanding we cease and desist, filing legal paperwork against us. At which point we have two options:
Ask for compensation and hope they're feeling generous, then "move" and change the name/scheme/skin/logos. (Your $250K option, assuming they'll go for that.) Spend a boat load of money we don't have to fight it in court, hoping to win a counter suit and break even.
Note that in the $250K case, we would "win", but at the same time would lose the right to the domain and/or continuing to do what we're doing here for all intents and purposes.
By spending some funds now to renew the minimal set in just the EU (or even just Germany), if a company comes along later, we get to: Force the venue in which the legal battle is fought to a place we have actual people on the ground (eg Germany). Have a very minimal cost for defense, since with an active TM it's an open/closed case that almost any lawyer would take it on for free, and counter sue for their expenses. I'd be willing to bet that a large chunk of that $250K "settlement" went toward legal expenses, since there were international court filings and such months before that agreement was reached. The guy involved probably walked away with very little in his pocket from this, instead being happy to not be in a crater of debt after initially holding out against a company with big pockets. But hey, you believe what you want and I'll believe what I want. I'm good with pitching in some funds for what amounts to a 10 year insurance policy. If you're not, that's your call. If we get enough in time, hopefully, it will happen. If not, well, that will probably go into the kitty and hopefully be used to ward off lawyers later if needed.
Cybersquatting (also known as domain squatting), according to the United States federal law known as the Anticybersquatting Consumer Protection Act, is registering, trafficking in, or using an Internet domain name with bad faith intent to profit from the goodwill of a trademark belonging to someone else. The cybersquatter then offers to sell the domain to the person or company who owns a trademark contained within the name at an inflated price.