OK, let's go step by step.
1. I don't understand your statement that the eSATA unit is configured as a "Slave drive". There is a LOT of misunderstanding of the terms Master and Slave. They a related ONLY to IDE ports and cables, NOT to SATA or eSATA. They are used only because IDE ports can support up to TWO devices on one port and cable, and so those two need to be identified separately. Thus on EACH IDE port there MUST be one Master device if it is to work at all, and there MAY be a Slave device, too. If there's a second IDE port, it also MUST have one Master and MAY have one Slave. There is NO such thing as a Master drive for the whole machine, plus slaves! The whole machine normally DOES have one BOOT drive and others for data, but it is possible (as OP has planned) to have more than one Bootable drive.
Now, IF you actually have an external enclosure connected to your machine by an eSATA cable, AND the drive inside it actually is an IDE type, then you do need to set the jumper on the IDE drive inside. HOWEVER, read your directions carefully, because I bet it MUST be set as a Master - after all, it is the ONLY drive on the IDE port INSIDE the external case. But I would guess that this is NOT your situation. So I'm still left not understanding how you could configure an eSATA drive as a Slave.
2. I am assuming that, aside from the 300 GB unit that is IDE, all your other drives are SATA. This would suggest that the IDE HDD is the ONLY drive on that port and cable. Hence its jumper should be set to Master (with no Slave present, if that's a separate choice), and it ought to be connected to the END (Black) connector on the ribbon cable.
3. There are two basic ways to set up dual boot options. One is to do as anonymous1 has done. You install ONE drive only in your machine, then Install a version of Windows on it. You remove that drive, replace is with another, and Install a different Windows on the second. You might even repeat for a third. When done, you re-install all the drives. NOW, whenever you boot up, you FIRST go into BIOS Setup directly and set which drive you want as the boot device, and it boots that drive's version of Windows. However, that means the that particular drive will be C:, and your other drives will have other letters assigned. But when you boot into a different Windows from a different drive, all your HDD's will get different letter names.
The other more common way is to let Windows do the work for you. BUT you must do it in a particular order. You must Install the OLDEST version of Windows FIRST. After it is all done, you can Install a different NEWER version of Windows (on the same HDD or a different one) AND you must tell the Install routine you want it to create the Dual Boot system. It will detect the older version and set up an automatic menu system. When the Install is complete and you go to boot, EVERY time it will stop at a menu and ask you which Windows you want to boot, and it will do as you say. This way keeps drive letter naming more clear and stable. I have NOT heard, though, of anyone who used such a technique to set up a TRIPLE boot option - I don't know if that can be done.
4. Given your plans, you will need to ensure in BIOS Setup that you have Enabled the IDE port(s), the SATA port(s), and the eSATA port.
5. In BIOS Setup there is a line for something like SATA Port Mode, with options like "IDE Emulation", "Native SATA", "AHCI", and RAID". You do NOT need to use the RAID option for your plans. The real device type for SATA drives is AHCI and that should be the setting for SATA ports in most circumstances. (In fact, many mobos do not show you a separate setting for "Native SATA".)
The "IDE Emulation" setting is for a particular situation. Win XP (in all its versions) does NOT know how to use an AHCI device, but it does have a "built-in driver" for IDE devices. When mobos started to use SATA drives, that became a problem. There are two solutions for it. One is to use a method that Windows Install has had for a long time: you must add in the proper missing driver for the drive device type you plan to use to boot from, reading it in from a floppy drive. Then the Install process AND the Win XP you install DOES have an AHCI driver it CAN use to access that drive type BOTH for booting and for running. Alternatively, you can set your SATA Port Mode to "IDE Emulation", and then you do NOT need to add a special driver. With that setting, your BIOS will intervene and limit the SATA drive to only the functions of an IDE unit, making it appear to Windows to be just that, and Win XP (and its Install routine) already know how to use IDE devices!
NOTE that this problem is NOT an issue for Vista, Win7, or Win 8 - they all have the IDE driver AND the AHCI driver "built in" so the don't need the BIOS to intervene in this manner. So, IF you are using any Windows AFTER Win XP, you should set your SATA Port Mode to AHCI and let Windows use the full functions of those devices.
In your case, OP, even if you want to install Win XP, you could just make sure to do that on the 300 GB IDE HDD you have. Then AFTER it is installed you will need to install the AHCI driver for your mobo in Windows XP (just once, usually from the CD that came with your mobo - read your mobo manual! - just like any other device driver) so it can use your SATA drives. In this sequence, Win XP loads itself from the IDE device it knows how to handle, and then, after it is running, it automatically loads the device drivers it needs from that same HDD (including the AHCI drivers) so it can use all its devices - all a perfectly normal process we don't even notice.
Check your mobo manual for another item. No matter which version of Windows you install, you may have to install from the mobo's CD the driver for the eSATA port. If you install two or three Windows, you might have to do this for each one.