For Non-Admitted carriers, the important item to then pay attention to is the AM Best rating (or equivalent rating agency).

Gifting equity in a house may be more trouble than it is worth if you are not near the life-time exclusion1) Potentially having to get the property appraised everytime an equity is gifted2) Having a title company update the title every time3) Exemption of the gift tax return is normally for cash gifts below the annual gift tax exclusion, you may still need to file if you gift non-cash4) If there is partial ownership over several years, having to properly pro-rate certain items such as real estate taxes, mortgage interest and rental income if the property is a rentalBest of luck 

This is true for bonus depreciation items as well.  

The property taxes will be on his Schedule A during the time the property was his primary residence, assuming he itemizes.

Have them send you a line by line item of what's needed.

Of course you can get discounts for having certain items FULLY updated, like plumbing.  

The other business I run is reselling, listing items on eBay & FB.

We understand that not every negative item we dispute will come off.We persist until we succeed because you must have a high-level of doggedness as a real estate entrepreneur.We understand there will be sunk costs and time being wasted.

I'm wondering how much specifics I need to include for each line item. 

The best place to start is with a spreadsheet that has every every cost itemized.