Can I expense materials the same year as I was doing all the work myself and the majority of work was mostly fixing non-working, absent, hazardous or leaking things (stairs, faucets, some plumbing/pipes, electrical, non functional door handles, some trim fixing/replacement, painting, blinds) in order to bring the place to rentable condition?

Not sure if it would be in the X or AE flood zone - I'm still looking for a good lot.If I went with the AE flood zone the elevation of the home wold have to be around 9'-11' and I'd want cement pillars. 

I'm looking for opinions / guidance on whether or not this is possible - from a city regulations stand point:The second floor of a 2 family has an attic space with stair access from the 2nd floor apartment.

The bridge is in rough shape and the engineering firm I had looked at it said that it would only support the weight of a pickup truck but would not support the weight of a cement truck or larger weights required for development or required by the fire marshal.

Insurance companies may inspect the property every year, and if they say "new handrailing by the stairs needed", fix it immediately, take pictures, document it. 

It’s was like $100 of pvc rest was labor and $5 of cement.

Sometimes we'll use a ladder to look into the attic if it doesn't have pull down stairs.

We just wall off the stairs connecting the two levels.

Put together a new foundation, new stairs, new everything rehab, basic stuff nothing fancy?

Yes, no stairs or anyone above you is huge.