Hello, new here from the Midwest and looking to start climbing. Within two years I want to climb Denali. I have some climbing experience from my military background, but not a pro. Any suggestions? Is my goal too steep for a rookie? Looking for a thoughtful discussion of how YOU started out. THANKS!

Get as much outdoor experience as you can.
- Altitude - IF you've never been up high try getting to the Rockies in the summer and hike some of the higher peaks (+13,000) to see how you react at altitude. IT takes about two weeks to get up to the 17000 ft camp, so if you are feeling OK on a high summit after just a few days of travel/hiking (and doing it a few times), you should be OK on Denali.
- Winter Conditions - TRy hiking and camping in the snow for multiple days. If you've never done this it'll be a new experience for you, even if you've done a lot in the summer months.
- Technical 'backpacking' - I thought Denali was a technical backpack, vs a true 'climb' where you had to surmount obsticles with rope and aid. TRy signing up for a week-long climbing course on a glaciated peak (Rainier, Hood, Baker, maybe Shasta) to get some experience on glaciers and ice, and with crampons, ice axe, etc.
As Puma Concolor mentioned, don't be afraid of going with a guide service. The only reservations I have of these is that they let some very inexperienced people on Denali trips (no glacier experience, no snow camping), so I didn't feel all that confident while hiking along the Kahiltna Glacier; the main 'West Buttress' route is fairly safe, but I was thankful when we came down that nothing happened (no crevase falls, etc).
- Get in the BEST CONDITION OF YOUR LIFE! jogging, bicycling, and thing to maximize your aerobic conditioning, and a little weight lifting or pushup/situps for upper body strength, too. The better shape you are in, the more you will enjoy it. I did Aconcagua, too, and thought Denali was much harder and exhausting on my body and mind.

I have nothing more to add, other than I did Denali after alpine climbing, winter mixed alpine climbing mountaineering (including two other trips to climb technical mountains in the Alaska Range up to AK Grade IV+), ice climbing, rock climbing, back country skiing, trail running, and lifting weights for 15 years. Denali was technically and physically easy, however, the historical weight of the mountain weighed heavily on me. Knowing that a dropped mitten or glove could mean losing fingers was difficult to face. The two men who died on an easy traverse earlier in the month weighed on me.

Make a plan. Climb big glaciated mountains in Washington and the Canadian Rockies. Go winter back packing. Take a specific expedition skills course. American Alpine Institute offers a good one and RMI offers one. Educate your self by reading. Freedom of the Hills, Andy Selter's book on Glacier Travel, Marc Twight's Extreme Alpinism, Climbing Fast, Light, and High should all be on your book shelf. Maybe don't read too many books on Denali, they can fuck up your mind a bit.