Work Comp Errors and OmissionsAuto coverage for Hired and Non owned vehicles if the PM does not have any vehicles titled in it's nameThere are several other coverage's you may choose to take, but the top 4 are the main ones.As you grow, you will usually pick these coverage's up as needed. 

So I guess to have a vehicle to write everything off it would have to be purchased or leased through the business.

Therefore, if you paid $20,000 for the car, and receive $5,000 for damages, your cost basis is now $15,000, which only affects your taxes when you sell the vehicle.

That would be crazy to split for example your vehicle expenses on 100 houses.

One day after he refused to move his guests vehicles I called the cops on him.

This is what I was reading..For passenger vehicles, trucks, and vans (not meeting the guidelines below), that are used more than 50% in a qualified business use, the total deduction for depreciation including both the Section 179 expense deduction as well as Bonus Depreciation is limited to $11,060 for cars and $11,160 for trucks and vans.Exceptions include the following vehicles: Ambulance or hearse used specifically in your business;Taxis, transport vans, and other vehicles used to specifically transport people or property for hire;Qualified non-personal use vehicles specifically modified for business (i.e. van without seating behind driver, permanent shelving installed, and exterior painted with company’s name).Limits for SUVs or Crossover Vehicles with GVWR above 6,000lbsCertain vehicles (with a gross vehicle weight rating above 6,000 lbs but no more than 14,000 lbs) qualify for expensing up to $25,000 if the vehicle is financed and placed in service prior to December 31 and meet other conditions.

S-corps are not a good vehicle to hold real property in general (double taxation), unless your s-corp is the member of an LLC.  

She will contribute annually $3,000 (3%) and the employer will contribute $4,000 (4%).Would you take advantage of this plan or would you rather do something else (SIDRA, solo 401k, invest it directly without going through any retirement plan vehicle, etc.)?

This makes is great tax sheltering vehicle but unfortunately it would not be of help to a W2 high income earner, you can only contribute earned self-employment earnings into this vehicle. 

Reduce living expenses, particularly vehicle and smoking/drinking.