My advise is start slow and learn about what equipment you need. Don't give up you day job until you have the clientel and equipment to cover you.
I have a compact tractor 2 yrs old 4x4 with bucket, low hours, a large tractor, equipment trailers and attachments, but less than 15K invested in all.
If I had to sell every thing tomorrow I would make money. Learn about what equipment you need and shop for the deals. Be patient. Learn how to take care of your equipment, running into the local dealer for everything will only delete your savings.
Finally consider small equipment more suitable to the task. The small tractor I just purchase was from a landscaper that decided to get more into installing irrigation systems. He had found that the tractor was too large around many houses and backyards. He was looking to purchase a Toro Dingo or Ramrod. The Ramrod is less money than the Toro. Everything can be transported on a small trailor and can be pulled with a small pickup.
A friend of mine has one for a stump grinding business has has on the side.

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