If so, were permits pulled & were they installed by a professional5.Are any of the homes rented to students6.Is there a flat roof7.are there asbestos shingles - Heating systems- PlumbingSome companies will not write properties with systems that have not been updatedThe Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policyc.

For example, a new roof is rated to last 20 to 30 years (depending the type of shingle used). 

Roofing and siding material that are considered modern are more expensive than shingles and lap siding(most common in our area). 

The places I have been looking at have asbestos shingles.

I would wait until the Tesla shingles are available.

Panels can be lifted up by hand, the ridge caps aren't actually ridge caps but someone bent metal pieces to DIY a ridge cap, the roof isn't vented, and no underlayment between the asphalt shingles and metal roof. 

The other reason I ask is the company I work for replaced a roof last year and I was told that if it was a replacement and not a substantial roof improvement it was an expense and not a capital improvement.In my mind this is a repair, because we are only replacing the shingles not the underlayment and it does not improve the roof design or type, and there is no improvement from the original. 

E.G. for roofing, we'll find the decking rotted in places, but we don't know that is for sure the case until the shingles are removed, and as such the insurance companies won't pay for it until we prove the damage exists.

Example for my market: - water heater $1600 (lower end of licensed plumber cost), 12.5 years (150 months) $10.67/month- roof (asphalt shingle) 2 br, 2ba typical size ~$10k licensed, 20 year life span $41.67/monthkitchen, exterior paint, flooring, plumbing, electrical, fencing, tree trimming (I have a property where the tree trimming is one of the larger maintenance/cap ex items at over $1k/year), bathrooms.  

I don't know your prices there, but a standing seam roof here is much more expensive than a heavy comp shingle so you might want weigh it against the end value.