@Troy Sheets are these GCing yourself, or are you hiring a contractor?

I currently hire a property manager for 5 MTR properties.

Once I hire a GC and they start their work, I need a Builder’s Risk policy with a “Theft & Mischievous Damage” rider or a “Special Form” policy.

The short version is this:  If you're willing to pay (considerably) more for the security of guaranteed rent, they are probably worth hiring.

Quote from @Jackie Liu: Hire someone to patch and paint the walls, then charge the tenant whatever that costs. 

It's better to hire someone else to handle this, but that doesn't seem feasible because you don't decide what should or shouldn't be done if the budget is less than $500.

Hired general contractor to renovate the home

Starting smaller might help you gain confidence and reduce potential stress.In your situation, if you're comfortable hiring a property manager to handle day-to-day operations while you’re working in the oilfields, going for the 4-plex could make more sense, especially with your high income.

No help from what supposed to be "the school" they have ignored me and I had to hire a lawyer.

Sure it can be a write off, but my question is if it is the highest and best use of your time (or the given employees time) to be running a skid steer - transporting it, storage, maintenance, cleaning, etc, and if it still makes sense if you need to hire someone to run it for you and take care of the other things.Add up all those recurring costs - maintaining the machine, maintaining the trailer, having a large enough truck to tow it, insurance and registration for all of the above, your time or your employees time related to all of the above...even at $14k a year it might be attractive enough to keep paying that and having them drop it off at the job site for you.A brand new machine could easily cost you over 6 figures - that's 7 years of rentals at $14k/year before including all the holding costs.