the boot manager way is prob cleanest but depends what you use and how you do it - will determined how easy it is
the way i mentioned above - i have all my o.s. 's in their own partitions , they cant see each other and each o.s. is it own c drive (so it is like there only one c drive and o.s. on the system when booting into any windows or dos)
the boot manager i used lets me hide or show which partition can see what (if you want have shared drive/partition for all the o.s. to use, you can do that) - so each o.s. has it own and one c drive
i also have the boot manager install on it own partition so if want delete any o.s. and start again, it doesn't affect it - the boot manager can delete the o.s., re-partition/re-size and re-format the drive and change the file system
the way i did for my dos 6.22 and win 95 dual boot - same way - remember oldest to newest - in your case it would be win 95 first then win 98 then win 2k and the games partition anytime really - just swap out my o.s. 's with ones you want to use
1- use dos 6.22 fdisk to partition and format a c drive - 2 gb max for dos and i made another 2 gb extended partition for a d drive for this o.s. (4 gb total for hdd) - in your case use any partition program
2- installed dos 6.22 (oldest o.s.) as normal
3- use super fdisk to make a 15 mb partition for boot manager and use the rest for for win 95 (36 gb of hdd) (but set the boot manager partition to active and save)
3- Install boot manager (Acronis OS Selector 8 ) (use the advance option to install to the 15 mb partition you made)
4- let the boot manager see the dos o.s. and it will add it to menu
5- go into boot manager settings - click view and click operating systems- right click in the o.s. name in green (not the partition name) (in this case it is dos 6.22) and go to properties
6-go to partition tab and select what other partition you made including the boot manager one to hide from the dos 6.22
7- use super fdisk again and hide all the partitions (dos 6.22 and the boot manager) - so only the empty win95 partition is left and set that to active and save
8- install windows 95 as normal
9- use super fdisk to un-hide what you hid before and save and put the boot manager installation disc in computer
10 - let the boot manager disc boot up and select activate Acronis OS Selector and take out the disc when done
11- repeat step 5-6 for windows 95
12- that's it
my windows xp/vista/7 rig was sightly different since i choose to install each o.s. on the own hdd - so install that as normal except for xp when i partitioned that hdd i left 120 mb of space for the boot manager and unplugged the power cable from each hdd to install each o.s. as normal and once i finish that, i put the boot manager disc in the disc drive, shut off the computer, plug the power cables in each hdd and turned on the pc and let boot manager boot up and install to the 120mb partition i made earlier and done steps 5-6 from above for these o.s. and same result