Dear XX:
These exterior pictures give a lot of information.
To make it clear, I will be using firefighter language, A side = street side, B side = left (clockwise from A), C=back of house, D = right side of A.
A side appears to suggest that there is no significant damage to the ridge beam. What you can see is sagging on both sides of the chimney rather symmetrically. Look at the distances between rows of shingles near the ridge in the photo.
B side images indicates that the up left part of the house was not built quite square, as judged from the unequal lengths of siding pieces between the left corner and window. I do not think the B side wall is distorted.
C side garage roof sinks a couple of inches over the rear entrance, and you can see that the back window of garage is distorted. On the other hand, the roof edge of the second floor remains straight.
D side the shed was heavily damaged, that might have reduced the force on the house from the tree. This is probably not salvageable .
General impression:
The house has been ignored for too long (much longer than the allerged 3 years since the condemnation). Remember none of our houses were as bad or even close. I would say this has not been taken care of for at least 15 years except for the front side. The required repair/restoration work for the exterior probably cost more than the structure fix due to the fallen tree.
Estimate of work:
1. repair the garage roof frame. I would put a 2000 for everything 2 days.
2. replace roof of house and garage. Material: about 15 square of shingles, probable 15 sheets of OSB for the shade side. Material cost: 2000 for shingles and tar papers, OSB 300, incidentals 200, total material cost 2500, labor hours 10 days including removal of old shingles and water damaged OSB.
3. windows: about 18 windows, material cost 3600+ 400 incidentals, total 4000. labor hours 6 days.
4. wooden trims, gutters, estimated 150 linear feet, material cost 1500. labor hour 5 days.
5. Exterior cleaning and painting 2 coats: Material 300, labor 6 days.
6. Ground cleaning, shed dismantling. Material cost: 100, labor 3 days.
7. cleaning: dumpster rental 600. 3 days.
Total: 11000. Add a safety margin, make it 12000. Total labor: 32 days.
Say if you hire some expensive handyman to do this for 500 a day (you probably can get a lot cheaper), this would be 28k.
