Is the property new or 100 years old, a condo or a SFR, are taxes and insurance among the highest or lowest in the country, is there an Hoa, do you use a property manager, if so what do they charge for, does your property have a tile roof and stucco siding or asphalt shingles?

Here are some pros and cons in my opinion:Pros: Desirable area, potential for 3 legal 2 bedroom apartments, new hot water boiler, shingles are ~5 years old, separately metered, lot is sloped toward back of building which allows for basement in-law suite to exit to ground level in backyard, seller to provide fire retrofit, parking for at least 4.Cons: Hasn't been updated electrically (2-prong plugs and 60 amp service), concrete stairway needs leveling (tilts toward house), in-law suite is not legal unit, older finishings in kitchen and bathrooms (and plaster walls).The list price is $399,000 but I wouldn't want to pay/offer this much.

If you needed to change the roof, would you go with IR shingles or not?

Asbestos shingles were used in roofing and siding as well. 

I noticed in the picture, the gable end still needs some shingles at the very top installed unless you have since installed them.

I plan to keep our house as a buy-and-hold rental property so I'd like to have a high-quality roof, but I am not spending $30k (our house is only 1900 SF, architectural shingle.)

I purchased two single family homes recently and both are in livable condition but I'm having trouble getting an insurance company to cover one of then due to some issues with the shingles and some dry rot.

Adding new decking and shingles onto the home (assuming it is NOT a flat roof) I'd expect to see you looking at $17,500-22,500 on the high side.  

I had a wind storm rip some shingles off one of my rentals a few months back, still fighting them and trying to get ahold of the "right person"Stick to it, don't let them not pay.

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.