You've gotten good input from others. A few more things to consider.
What is your feed-out rate going to be? You need to have a small enough exposed feed face, so you feed out faster than spoilage can occur. This is part of the silo/bunker/pile design.
Since you have a loader, you can use that to feed with. Is it reliable? An old relic? If you go this route, you're feeding system has to work, even in the middle of winter. Since you're in Ontario, this is a definite concern. With bales, worst case scenario is you get help to haul them down/feed them.
How much acreage do you want to put up? Are you having problems with the bales now? Is there a specific reason you want to go with silage, other than the ease of harvesting? (NOT a minor concern...)
IF you have the equipment, silage/haylage can let you harvest more acres with the same amount of people. You're just substituting equipment/capital costs for labor costs. There are a few drawbacks, however. If you bale at the proper moisture, bales are fairly foolproof. Don't let them get rained on, don't stack them too wet, and they're good feed. Silage, on the other hand, takes knowhow and management to get right. It's much easier to mess up, and have bad feed. You can make some very good feed, and it'll go bad if you don't store it right.
If you're really interested in how to properly make silage, do your research. One place to get recommendations on silo/bunker/pile design, and the requirements for packing/density is
Dr. Richard Muck of the Agricultural Research Service. Your tax dollars at work. Dr. Undersander of the Univ. of Wisconsin, Madison is also a good person to google for silage info.
If you find you really want to go for it, and need some additional help, drop me a line at
michael.boettcher@ars.usda.gov and I'll try to point you in the right direction (or at least what I think is the right direction is...

)