If they see you have disposable income, they will come at you hard to invest more money into their training and software programs. 

The crane, the labor, disposal, insurance, I get that all that costs money but I highly doubt labor costs have gone up that much in 3 years... the company isn't giving out big raises if they are worried about inflation costs.

I’d second everything he said.In Texas, landlords can deduct from the security deposit for damages beyond normal wear and tear—but you need clear documentation.

Wow it sounds like we are kinda "brothers from another" haha.It is extremely rare to find Millennials that are into Wright much less Rand :).

Demolition and removal of the old roof may cost between $300 and $500, including disposal fees. 

Quote from @Bob Avery: I know this is contrary to a lot of the opinions on this forum, but if you consider the common case outcome rather than the best case outcome, you would probably be more successful in real estate if you choose engineering/medicine/law/business as a profession and real estate as a hobby (with tons of disposable income to dump into down payments and banks willing to lend you money) than you would be if you choose real estate agent / property manager as a profession.Totally agree!

How to shut off power/water/gas, change furnace filters, lint catchers, batteries, garbage disposal, toilets (flushable wipes are actually not flushable) etc- we emphasize to report problems and we always thank them first when they do.

How to shut off power/water/gas, change furnace filters, lint catchers, batteries, garbage disposal, toilets (flushable wipes are actually not flushable), how to reset a GFCI and why did it pop in the first place etc etc We have a checklist for this.- reporting: we emphasize to report problems and we always thank them first when they do.

@Nina Diehl  depending on the condition of the grill either dispose of it or you can just gift or token sale it to the tenant renting if you know it works.

A full page on security deposit charges for disposing of furniture.