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

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.

If you’re willing to do the work as well as a professional management team for the same price he can keep some money “in the family” by hiring you. 

You will likely have to hire/fire a few times over before finding your final hire.

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. 

And if possible, they can even hire someone to clean up the property and then pass the bill on to the tenant.

Build an SMB on top of your real estate (the reverse of #2)Short-term rentals and high owner-participation real estate businesses can have great returns.Obviously not for you if you just want passive RE.We are in the deep end here, where each case should be judged on its own facts and merits by your CPA.You should hire a professional to review your particular situation before you make an investment.

It is important that you hire professionals who have experience working with foreign investors.

With the amounts you are talking about, I would probably tell you it's worth hiring someone to do this for you.  

Every area I know has gotten worse and worse and worse on it.Fifteen years ago,  when I was buying, rehabbing houses and holding, I oculd hire a licensed contractor and they were able to change toilets, faucets, even water heaters.