In his experience, for this job he says we don't need a permit and it will only cause more delays. 

This is my first investment property so I feel more hesitant about going into rehab work than something fairly newer or even older but with minimal repairs/recently renovated.

This way, you would be paying for the roof as part of the property purchase, allowing you to claim the tax depreciation once you take ownership.Delayed Closing with Roof ContingencyAnother approach is to add a contingency to the closing that allows you to replace the roof before closing but delays the actual closing until after the roof is installed and insurance is in place.

**Loan-to-Value (LTV) Leverage**: Lenders might be more willing to take a second position if the combined loan-to-value ratio is conservative, meaning there’s plenty of equity in the property and the lender’s risk is minimized.5.

But if you prefer stability and want to minimize future risk, the conventional loan provides more certainty.Ultimately, the decision depends on your cash flow needs, risk tolerance, and long-term strategy. 

This is called delayed financing.

Many projects go over budget due to unforeseen repairs or delays, and having a financial cushion is critical to staying on track.4.

and most of the time is  bad management, bought the wrong price, Interest and Insurance to the roof and, I cant get out the Bridge loan to do a DSCR loan etc ...Simple hands on, work do research and minimize risk. 

They are young, still in college one more year with minimal income.  

A few things I do personally for clients is: create a P&L, market to my buyers list, pre-market the property online where the target audience is, and make a plan for bookings and the booking calendar to minimize losses while up for sale and operating simultaneously.