Best bet is to get inspections and or professionals out to assess the systems and provide estimates.With the roof 20-50 years depending on the climate, area, type of shingle and type of roof.

Regus might let you hang a shingle for a fee without much need for an office, I'd ask.  

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 The 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.....There are many endorsements that are available on the homeowners policy.

There is a soy bean oil product that can be sprayed on composition shingles and it makes them plyable again.

The only folks that can afford to buy from wholesalers right now are the ones that have their own contractors and buy roofing shingles by the truckload.

We cash flow 300 to 500a door and I'm still shingling roofs.

The roof is fairly new, half metal and half shingles.

They did a survey at the property and find out there are some lifted shingles on the roof.

The list you have there, assuming the work was completed professionally (architectural shingles, good quality kitchen) and barring destructive tenants (which seems not to be the case) sounds like he put about $70K in already.  

You may also be held to additional standards which could cost you more money than intended (i.e. some shingles come off or some of the vinyl siding gets cracked.