Many experts will confirm that the larger the tree, the longer it will take to get established, and that a modest sized tree will outperform the huge transplant in 5 years.

"As large as you can get them" - that depends on your budget. Anything up to a 4" caliper (trunk diameter as measured 12" from grade) tree can usually be moved around by hand. Cross that 4" mark and the cost makes a big swing due to 1) equipment needed and 2) smaller quantity of specialized stock. We quoted an 8" caliper tree for a client and between the tree, delivery to site, and the crane to set it, we were at around $5k.

As for specific trees, your local county extension office can give you some great advice for what trees are most successful in your immediate area. According to google, this is your local extension office: https://extension.purdue.edu/monroe

I bought some pretty large trees for instant shade in my first home but it wasn't cheap.

I'd just spend all winter researching specific varieties, how the sun moves, how you plan to use various areas on the property, optimum placement, proper planting and watering techniques and then get as large as 1) you can handle yourself and 2) can actually find locally.

Once you bring in the heavy equipment the cost really starts adding up and as laceyvail mentioned the smaller trees usually establish more quickly and do better over the long run.

I think you would be shocked, actually, at how quickly some trees grow just from seed. They seem to do especially well since the roots are never disturbed. Many smaller container trees do well, and the "secret" to getting them going is often regular water during their establishment period. Genetics plays a big part; many species grow fast as is their nature. However, many GOOD trees are not the fastest growing. In the long term I think you'd be more happy with selecting quality species/cultivars and be patient. As soon as we get busy with life, trees have a way of becoming huge while we're distracted. Most people can barely keep up with the proper pruning that making a good tree requires.

What others have said about the cost of larger trees is right on.

Sometimes large native trees are not expensive. I handled the construction of the drive and parking in this photo. The photo is from 2016, construction was in 2000. I hired a tree spade service for $1000 per day with no guarantee of tree life. I had authority to remove trees from a forested area about a half mile away. The plan called for pines and we moved 18 trees of about 15-18ft in height in two days.

In the photo compare the trees to the cars in the parking lot. They are now 16 years later about two thirds of mature size.

We have 4 huge maple trees at the country house. They’re about 100 years old, look pretty cool

American persimmon tree can be very tall. Have you thought about fruit trees? You have room for a small orchard.

Pls8xx, nice to see you r here again. You've provided a lot of good info over the years.