Well I live in NE Wisconsin so I start my plowing around the last week of April if it is dry enough. After about a week of working my land I normally wait a few weeks after the local farmers plant their crops which is usually about the 1st week of May. I want my crops maturing after theirs so I try to plant mid May.
I use all round up ready soybeans and corn since my fields where once used for spreading liquid manure years back when my aunt owned it.

Foxtail is thick our there if not sprayed. When my corn comes up about 12" high I have a large boom sprayer on my tractor with 110 gallon capacity and go to town spraying.
I own a small (38hp) tractor with implements that I have picked up over years. I have a 2 bottom plow, 8' disc, cultivator, 5' brush hog, 12' spring tooth, cultipacker, 110 gallon boom sprayer and a John Deere 2 row corn planter. Took me about 4 years to find all this stuff. Before this I borrowed my father-in-laws stuff. Was a hassle but it worked great until I broke his tractor.

The Mrs. said "no more"!!!! Go buy your own stuff.
Clear your brush as soon as you can get on your land. I would take a soil sample to find out your PH. You might not need lime??? You will not know if you do or how much until you get a sample. I would not spray until everything starts to green up and really start growing. Round up only kills growning plants not pre-emerging. You can purchase pre-emergents to spread but I use a generic Round up. I buy 5 gallons of Razor Pro. Can buy that for about $125. 5 gallons goes a long ways.
You can lime as soon as you get your results back. I used pulverized lime since it is easier (smaller) and will work with your soil faster. Proper lime allows your plants to adsorb nutrients.
All my stuff is planted mid May unless I plan on saving an area for a fall planting. Then I will plant oats or rye there just to keep the weed out. Come about Mid August, I work up that area plant my rape & turnips. About 2 weeks later I walk thru with my oats and rye and seed on top of my turnips. I want my oats no more than about 10"-12" high when they stop growing.