Sounds like an internal policy decision that you will never win, regardless of any reasonably prudent measures you take.

I wanted to learn how to build and fix interior construction.

I would get a roofing contractor out there to pull back that roof and start to source the probable, and you'll need to mitigate that issue then move to the interior work to get the drywall/insulation fixed. 

The interior and grounds need a major renovation, which I am estimating at around 1MIL.

Do you have pictures of the interior of the property? 

The interior is finished with pine paneling to give a warm and inviting feeling of cozy comfort. 

For interior alterations, The City's website states that I can submit a RAAC Document (attached), Residential Automatic Approval Certificate, acknowledging that no plan review will be conducted since the drawings will bear my stamp and signature.

We've also done all the maintenance and repairs all these years, we put new linoleum in the kitchen, painted the interior, built a new fence/gate, stained all cabinets, much more all without reimbursement as the owner is a tightwad and had never wanted to pay for upgrades.

Oy, I have to remember to measure the interior sill height, from the pictures it looks like less than 2' probably 23" lolDid I mention I'm considering installing a 30" deck under the window to make it less than 20'.But I would still have to deal with the other side. 

We replaced floors, repainted every inch of the interior, and fixed everything that needed attention.