Answers

Call a professional certified roofer who can do a full inspection and report of how to proceed. Professional roofers can bring insite and cost savings others might not. They have years of experience and a trained eye to make sure all problems with a roof are discovered and remedied! Remember - When hail hits an asphalt shingle it often knocks off the protective granule coating. Once the granules are gone, the protective layer underneath is exposed to the elements. Always call a professional roofer!

If actual damage has occurred to the roof, due to hail, there is really no other way to fix the damage, except replacing the roof system.  

Depending on the type of roof that you have, if the damage is minor, you might be able to complete a spot repair, but that also depends on the condition of the roof.  Hail typically falls randomly over the entire roof, so when there is damage, it tends to be all over.  If your roof is older, it might not be in repairable condition, or your roofing material might have been discontinued and have no match available for sale.

I suggest having a Haag Engineering certified roof inspector or a structural engineer evaluate the roof and tell you if you have another option.  

I would rather think your gutter needs a good sealant. If your soffit is sagging, you have some structural issues.Most likely nothing to do with the gutter. 

The most important thing would to review its structual integrity. This can be accomplished by removing some of the soffit panels and taking a peak inside. It could be a a rafter tail is comprimised or broken. Therefore, it would need to be fixed by lifting and sistering. (placing dimensional lumber beside the rafter tail and fastening together). Another fix would be to install a column to support the roof. Installing the column would require a stable footing below, (a concrete pad) and lifting the roof to the proper slope and affixing the colum to the sub-fascia board on the eave. The column method would provide the best support over time and combat heavy snow loads, however a "post" would be in the walk path most likely.

Thanks for the valuable information.

What did you decide to do then? Following the proper process would help.

You can proform both jobs at the same time if you are good at what you do. I have in the past grinded a Grove in the brick chimney all four sides then used a brake to bend a little half inch lip on the top of my flashing metal flashing into massonary Grove then caulked you will never ever have to worry about again in your lifetime Only reason I did massonary work first is because I didn't want to get my shingles all dusted.

The masonry work should be performed prior to repairs to the existing roofing, unless the roof is leaking, whereupon you may need to make intermediate repairs to stop the leaking while the masonry work is performed.

Masonry work first. Best, Ken

Definitely before you do the roof, masonary work and any flashing around the chimney should be done prior to starting on the roofing.

Our recommendation would be to do the massonry work first and then roofing for a few different reasons.

1.This gives the masons freedom to step and walk on the roof without causing damage to the new shingles. 

2. You will want to make sure the new flashing that is intstalled around the chimney is installed correctly, accounting for any masonry changes and is not damaged due to installation.

3. Ultimately, that the new roof is not damaged and that the warranty does not get voided. 

It is always better to repair the chimney prior to any roofing work. This way the new roof doesn't get damaged.