Good advice as usual from Mettelus. FWIW I'm pretty sure the looping is now fixed.
Really I think there are two issues: Stability and cost of maintenance/updating.
Windows is highly cost-effective but only if tweaked properly, and the causes of issues are not always obvious. Even if you have a clean computer, install Windows 7, then install SONAR and use only 64-bit plug-ins Windows can still be problematic due to interactions. It took me
years before I realized how much the "HD Audio" codec installed by my graphics was impacting performance and limiting the ability to get low latency. It is extremely frustrating to find out something like having a floppy disk port enabled on your motherboard by default but no floppy drive present can cause problems. It's also frustrating that the more a program depends on Windows for performance, the more likely there will be problems. Often cross-platform programs can be more stable, but at the expense of some level of performance hit.
As to maintenance and upgrading, having been raised in the days of tape I have a somewhat different perspective. A four-track recorder with nothing else cost me $2500 adjusted for inflation, and I had to keep dishing out at least $50 per month for tape. The option was renting time at some studio that had probably $100K-$250K worth of gear. Today's DAWs, including SONAR, do pretty much everything those studios could do from a recording standpoint (e.g., excepting acoustics, room treatment, etc.) and for me, spending $150-$200 a year to maintain SONAR in peak condition isn't that much more than replacing my strings every few weeks. Also remember that while many updates are about bugs within SONAR, many are also about issues caused by interactions with other software or Windows itself.
None of this is to minimize the frustration that happens when your tools aren't working right, I've "been there and done that" and it sucks. However, it's what I tell myself when I need to remember that all things considered, running a computer-based DAW is a big improvement over what I was dealing with 25 years ago. I'm very grateful my system runs so smoothly and I can count on SONAR to get the job done, especially since the upgrade to Platinum. But, I attribute a lot of that to the hardware platform.