I think I understand what you are trying to do, but I'm a little unclear as to how you plan to "hotswap" your HDD. I'm also not sure if you intend to have OSX and Windows on the new HDD, or just Windows. I wrote the majority of this answer assuming you wanted both.
First, some clarification, just to be safe.
A. Hotswap generally means exchanging drives while the host machine is still powered on and potentially using them. This is usually only possible with some RAID arrays using data redundancy, whereas a Mac generally only has 1 HDD with no redundancy, and it would be very unhappy if you removed it while the system was running.
B. When Windows is installed via Bootcamp/dualboot, it exists as a second partition on the same disk as the OSX partition. You see 2 drives in Option boot (like in your screenshot), but it's just 2 partitions on one disk. When this is the case, Windows will obviously not boot with the OSX disk removed, as this is also the Windows disk.
C. A Mac can boot to a properly installed Windows partition without OSX ever having been present. It's all just Intel/ATI/Nvidia hardware, same as any other PC. Your only challange will be finding Windows drivers for the Mac-flavored hardware. There are many writeups on doing this.
Regardless, your only choice will likely be some variation of cloning.
Basically, just clone the old HDD to the new HDD and install it in your Mac. You will have the exact same operating environment on the new disk, as if nothing ever happened. If it fails, your old disk is unharmed (provided your select "target" and "source" properly). To begin, place your new drive in an external USB enclosure, and use it as the "target". Once finished, swap drives.
I have successfully cloned modern flavors of OSX with Carbon Copy Cloner, Clonezilla and Norton Ghost 11.5 (people also rave about SuperDuper). I have read Disk Utility works as well. CarbonCopyCloner and SuperDuper (and maybe DiskUtility) are usually the preferred method of cloning OSX, but I'm not sure if it will pick up the Windows partition (it should...).
Test aftewards to be sure everything worked. You can boot your system off of the external USB drive and use it just as if it were installed internally (just a bit slower) by using the Option key at boot and selecting the proper drive. Once you have verified everything is working, take the new HDD from the enclosure, place inside Mac, and place old HDD inside enclosure. File old HDD away for safekeeping.
From here, you can stay with your old installation scheme on the new HDD, or update the operating systems as you please and boot from the enclosed old HDD whenever you need access the old Apps. If you want to get hardcore, you can look into creating a virtual machine from your old HDD's image.