Welcome to the site from another guy from Lake County.
Winter here isn't tooo terrible compared to other places. At least ours won't start for a few more weeks. I was in Minnesota for work a week ago. My flight home was delayed 2 hours because of snow - flurries at that (and a little runway construction). They had about 3" the week before that. Denver and the mountains were a mess last week from what I saw on the news.
Your building sounds like a fun project.
$50k for 2016 sf is around $25 a sf which seems reasonable not seeing the complete specs he is quoting.
Don't know what your timetable is but as wet and cool as it's been here the last month or so, I'd wait until spring to break ground unless you get a great window in the next couple of weeks with warm dry weather but my guess is that you can't turn a permit around in that short of time.
Will your permit be issued by Lake County or Crown Point (or Cedar Lake, Lowell, St. John, Schererville, Merrillville, etc. as the case may be)? Make sure you know which set of rules you'll be going by from day one and what those rules are.
The big one for you to know about is how they will figure building height. Some use eave height and some use the average of the eave and ridge height - both have limits which will vary. Some will tie the max building height to the home's height, other's will not. 2016 sf and 22' high may not fly depending on your zoning and size / height of the house on the property. Need to talk to the appropriate building department ASAP and get a good handle on things. There have been members of this site that have had to tear down roofs because of a mis-understanding between them, the contractor, and the building department.
36' or 40' span open garage is the perfect application for a trussed roof. Your intended ceiling height would pretty much eliminate the possibility of attic trusses though.
Metal roofs on average last a lot longer (up to double or even more) than a composite shingle roof if installed properly but you will pay a premium for that up front. By installed properly, I mean that you need to match the panel to the roof pitch, and install the complete system per the manufacturers specs including roof sheathing, underlayment, panel attachment clips, panels, trim, and other miscellanous accessories. You're insurance company might offer a discount for a metal roof. Incorrectly installed, it can be a nightmare to find the actual source of a leak under a metal roof.
ICF foundation is overkill for this application and climate. Finish basement in a house - yes. Pole barn - no. You won't see an energy savings over typical poured concrete and some rigid foam perimeter insulation. Install 2" rigid foam vertically along the interior face of the foundation wall and under the slab for 4' around the perimeter of the building.
How big of a toy hauler are you considering? Plan the slab thickness around that vehicle's weight at least for one bay where you would park it. You're also going to want to thicken the slab under the posts of the lift.
If it fits in the budget, I would want radiant heat. From a friend's similarly sized building near Joliet, you won't need extra heating if the boiler and pump are sized correctly. You will have to make sure that plan your lift location accordingly to keep tubing from under the posts and the guy doing your saw cuts in the slab knows exactly how deep the tubing is. The concrete guy will hate you but any slab (especially with radiant tubing) needs to have the mesh installed on chairs to keep it in a constant position throughout the slab. Mesh in sheets instead of rolls also helps this. A couple / few ceiling fans would help both in summer and winter.
As far as lighting goes, either get fluorescents rated for 0 dgrees with electronic ballasts or even low bay metal halide. You'd have to have someone do a point to point lighting calculation to determine which will be more efficient.
I've had a Rust Oleum Pro 2 part epoxy system in my garage for going on three years with only two little areas just now starting to fail. I would consider the Sherwin Williams system if I do it again - especially now that I get about 30% off on all SW products through work. There are a lot of positives and negatives to the various systems that guys on this board have used. Definitely a lot of info here on that subject.
Some other things to consider:
What are you planning for siding, windows, man doors, and overhead doors?
Are you planning any floor drains, or other interior plumbing? How does that affect your septic system (assumed from your statement about unincorporated Crown Point)? Shouldn't affect a well unless you plan to use a lot of water in the building.
Does your house's electric panel have enough capacity to feed a subpanel in this building (present and future needs including heat, beer fridge, compressor, welders, large table saw, etc.) or will you need to get a new service from NIPSCO? If you're trenching power from the house to the pole barn, run an extra empty conduit in the trench for future use for phone, cable, etc.
Same for gas service. I would think that NIPSCO would want to run a separate service for that building but I could be wrong.
What type of lead times does NIPSCO have for new service installations or modifying/upszing current services if that is the case?
Is any of the building going to be used as an office, washroom, man cave, etc.? With the height you're planning, you should be able to get a usable storage deck and room for a compressor, radiant heating boiler, off the main floor yet fairly easily accessible for service.