re: Is there a such thing as skidsteer skill training courses?

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hell I’ll hire you. Come to Hammond with a skid steer with bucket and grapple you can practice all you want while clearing brush and pulling stumps

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I think this is the answer here. Take small less complicated jobs that aren’t in a time crunch to start. Get paid to learn and increase your skill.

Or find someone who does it for a living and go work for them for 6 months.

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I am scared to take the plunge. I worry about the obvious issues but I think the real hesitation is the initial buy in

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Being scared to take the plunge speaks to an understanding of the risks involved and is a healthy and possibly good way to avoid some serious financial difficulty...it is smart to be concerned.

The initial financial layout for the type of business you are talking about is not small....it is substantial. The upside is it is entirely possible to rent the equipment, have it delivered, and pass the costs onto the customer...if you own it you are going to pass ALL costs along to the customer, renting it is arguably cheaper than owning....especially if you are not also a mechanic and even if you are making repairs and maintaining equipment is another business which may interfere with your ability to perform your actual business which is operating equipment. The problem is there are an awful lot of people who do own the equipment who will do the type of work you are talking about for a price that does not account for the cost of the equipment....they do not stay in business long but their equipment winds up in the hands of another person making the same mistake....thus making it hard to compete. There are also people like me who have some equipment and do small jobs for cash who aren't really in the business to make a living but do some work for others to offset the cost of owning the equipment, if that makes sense. I am not in it to make a profit I am in it, on an extremely limited scale, so I can have use of a tractor and dump trailer when I need it without paying for it entirely out of pocket. This is not unusual, especially in more rural areas.

Finally one word about owning equipment meant to be used daily in a business. I did this for 14 years. I owned a Ford 550 backhoe which had been more or less completely restored, a 18 HP Kubota Backhoe Loader, a Ditch Witch trencher backhoe combination and 2 Ford Line trucks (derrick digger, bucket and crane combo). The 550 was hardly ever used because transporting it was an event. The Kubota and the trencher were used almost daily and the trucks were used at least once a week. When there was something wrong with any of it I would have 4 or 5 electricians, making about $55 an hour in wages and benefits, standing around trying to fix the equipment. None of them knew much about repairing equipment, they were excellent electricians but lousy diesel mechanics or hydraulic mechanics. I eventually subbed ALL of that type work, to other people who owned the equipment and had all of the headaches associated with owning that equipment. I even sold one of the line trucks to a young man who I then hired to do the work for us when needed.....it was FAR more cost effective. What you are talking about doing is ideal for that....there are a BUNCH of contractors who need a few days or hours of that type of work who would far prefer hiring someone else than keeping up equipment.