First cylinder set I bored was a 1966~67 Honda 160 block to take 175 pistons. I think I used a Bridgeport but it was so long ago I forget (around 1974)
Since then, I've done literally thousands of motorcycle cylinders.
I taught cylinder boring as part of 'Clinic 3- Machine Shop' at Motorcycle Mechanics Institute, Orlando for over 3 yrs (so several thousand students) Almost everyone could bore and hone a cylinder to within specification of +/- 0.0002" by the end of 3 week course (at least all my classes) The problem with boring on mill is lack of quill travel which is usually 5" or less. A lathe can sometimes be much more useful if you have a large enough bar. It would be better to make something that will bolt on in place of tool-post and take a 'spring cut' or two before honing, Bar should be 2~3" steel to give greatest accuracy, use croos slide to set cut. The KLR cylinder doesn't need torque plate, do you mean to bolt it to a face plate? If your not familiar with using DTI it can be a pretty frustrating experience to get things centered up properly. As for poster who said torque plates probably aint needed, correct but some engines MUST use torque plates as they 'distort' the cylinder to fitted shape (Harley Davidson 'Evo' cylinders distort around 0.001"~0.002", center gets 'smaller' when fitted if torque plates ain't used) You will need a rigid hone (Sunnen, Ammco, etc) to finish size cylinder accurately, the 3 leg spring hone won't work to remove any out of round or out of parallel. You'll also need a bore gauge, the cheap $50.00 ones are not worth the money, you need 0.0005 " resolution minimum, 0.0001" is way better (and 'only' about $175.00 more expensive)
Initial set up may be substantially more than paying to have bore done but it will repay investment many times over when you start doing modifications (swapping cylinder liners, 'big bore' kits, etc) I would probably try and find KLR300 piston spec to see if it could be fitted into 250 cylinder.
As for doing 883 Harley, no idea how many students did their own before HD stopped supplying pistons (hundreds of $125.00 piston kits instead of $800+ piston/cylinder kits) You have to remove 0.495" from bore to go to 1200cc, makes cylinders a LOT lighter. Modified 883 head is actually 'better' than stock 1200 head, there is enough material to make ports a much better shape and size (and way cheaper than buying Buell 'Lightening' parts)