If the one lender won’t, the next one will just wake sure there is no deferred maintenance.

From the info presented here he's a crook. " likely copper bad too"??? 

That means you’re in the driver’s seat, deciding what needs to get done for maximum value, versus what can be deferred until later.

Fast forward to present time, I never got to complete the house and lost over $200K on the deal. 

Under the involuntary conversion rules, my understanding is you could defer gain recognition on the insurance payments if you reinvest in similar property within a certain timeframe, but that doesn't interfere with taking a write-off on the old roof's remaining depreciation through a partial disposition.

It's not the most exciting part, but future-you will thank present-you for being prepared.

Many flippers use private investors to fund deals, and structuring the arrangement properly is key to ensuring both sides feel secure.When pitching a private investor, the most important thing is to clearly present the deal.

What they will do if your DIY-ed cost segregation is audited is they will send you an engineer (you pay travel costs) to conduct a "real" cost segregation study and present it to the IRS instead of yours.5.

All normal capital invested that was not generated from a gain that you deferred is still subject to tax.

If it's vacant and really needs cleaning/repairs, then I'll wait until it's more presentable.2.