I’d also second the concerns about why this land isn’t in farmland already. There is a lot of land in the Upper Midwest that is absolutely terrible for farming and a long, long way from those specialty, high value markets that you must have.
On draft horses being difficult, dangerous, and expensive to feed. No more than any other horse (aside from the feed). However, that being said they are intimidating, very much so. They are also naturally far more destructive, they like to push on things…hard. So I guess they are more difficult and expensive! But the danger comes from not knowing what one is doing with a horse, any horse…or, in farming from those long hours and just taking a short cut this one, last time, because you need to get the field finished.
To give you a sense of size. Here is a picture of my husband and I playing around with my big guy’s harness. I’m 5’4", my husband is 6’3", and Buddy is considered to be a small, small Shire.
Thanks for the questions and giving me some things to ponder. The area here is pretty different, I say this because more people leave each year than move in, it is very remote, very low population, it is snowing around 1/2 the year, and people do not have a lot of money nor do they have good paying jobs. Most people here just want a camp in the woods and go there for weekends or to live there. However, there are some 100, 150+ year family farms, there may have been more farms in the past but no one stays here or would have kept the family farms going, only a select few remain.
I don’t mean to sound overconfident in wanting to undertake this, I do understand the work and time, and the length of time to complete a project like this. I am not naïve enough to think I can knock this out in a week or summer, it is something I would like to do piecemeal over time. I don’t plan to clear the whole 100+ acres, rather, enough for pasture, some crops, chickens, maybe other animals as time goes on. Perhaps, homestead or bigger hobby farm is the best way to describe it rather than farm.
Buddy is lovely!
Do you know if there is hay available already to purchase in that area for your potential new draft horses if everyone is leaving?
Also, there is a good group on FB called “Market Gerdening Success Group” that has a tonne of valuable information.
There is hay, but there is always tons of it listed on craigslist and other internet sites, so I think it would be readily available and accessible.
The ag agents should be able to help with soil quality and testing, what types of crops would the soil and your climate support, etc. They are not going to be much help with the ‘farming with horses’ aspect.
Maybe if you give a general area of where you’re thinking of buying land, some here might have more advice for you. I went back and re-read your original questions of which crops to plant and
also that you would like to make this your full time living at some point.
You might want to join some Homesteading internet groups- they are a wealth of information for people who’ve been there and done that.
Just dig a big hole and drop bank notes in it. Less work. 
I live in Wisconsin (west central) and have neighbors who remember working with horses when they were young. I would suggest you look for a listing on the internet not too far from you that is having a field day with horses. They will be demonstrating farm work with draft horses and the local one here is extremely friendly and quite willing to help a newcomer. If there are no field days then consider going to the county or regional fair as they will very likely (at least in Northern Minnesota and Northern Wisconsin) have major draft horse classes and the folks showing will be able to give you useful advice.
Thanks! I have seen that documentary, it is on prime as well, was excellent. Now, if I can get some Martin Clunes type money ha!
@Hopefulfarmer There’s a large Amish community near me in Iowa in the town of Kalona, and there’s an active auction house there. Might be a good place to find horses and/or gear.
The next draft horse sale is in April: https://www.kalonasalesbarn.com/draft-horses-carriages-antiques/
