The equipment is decently priced & you get discounts up front for signing up.

He's also got a 5-7 stall horse barn with tack room and a large tractor/equipment building with A/C office space. 

The cost from year 6 on tends to be more as machines and equipment some start winding down their useful life expectancy.

Fishing equipment. 

From the pictures, all the equipment has been ripped out and looks like a "clean slate" inside.

When working with lead I used proper equipment, HEPA filters with a properly fitted half-face mask, and used excellent hygiene (washing/showering, not eating, not smoking, careful handling and so on) and still became lead poisoned. 

While you need to be responsible and not spend money you don’t have, sometimes a nice dinner or a new piece of equipment you have been wanting is all you need to give yourself a boost.

@Joseph PuglieseIf your business is accrual basis and previously accrued the revenue and included it in taxable income, yes you could write off the bad debts.If cash basis, you don't get to write off revenue you never received as you never were taxed on it in the first place.There are extremely limited exceptions to this, particularly if you're cash basis and recognized the revenue under constructive receipt, however I suspect your fact pattern is not that complicated.You can deduct your normal operating expenses of the rental.Your CPA is best equipped to help you deal with this.

He has a 1car 2nd garage right in the corner of his lot for lawn equipment and no good place for a bigger garage.

That is enough to maintain a lawnmower and other equipment and tools.