I want to do things the right way, but feel the pressure of a tight budget that will get drained considerably by the permit fee and multiple inspection fees. 

We have a tight 35 mile radius around columbus and 4 cities in florida (Tampa, Jacksonville, Orlando, Miami) with the same radius.

The deadline to file with the county is May 17th.

If per unit, then it'll be tight to cover after all your expenses.

So welcome to the "New-Norm"; NEO-Stagflation: Throttled HIGHER price, throttle higher inflation always on cusp of breaking out to run red-hot and verge of cooling but never going either, lower volume, tight labor.... 

I have tight deadlines.

@John WilliamsBuy right and sit tight.

Charlotte market is hot right now, inventory is tight, and building is just now starting to catch up. 

"That" alone (the age of it) may come into play soon, as most ins co's are getting very tight on the coverages and policies.Without seeing it, but knowing the climate, I would lean towards replacing the roof ... with a decent but not high end product.

Just drag your feet on everything up to their deadlines as much as you can until your house is sold.