Insurance is the most boring and most important purchase a contractor makes. The right policies turn a $50,000 mistake into a phone call. The wrong (or missing) ones turn a small claim into a closed business.
GL covers third-party bodily injury and property damage caused by your work. Standard limits are style="max-width:780px;margin:0 auto;padding:48px 24px;font-family:system-ui,-apple-system,sans-serif;line-height:1.55;color:#0f172a"M per occurrence / $2M aggregate. Almost every customer requires evidence of GL via a COI before work starts.
Most states mandate workers' comp from the first hire. Premiums scale with payroll and the trade's risk class — roofing and demo are expensive, painting and finish carpentry are cheap. Sole proprietors and 1099 subs usually aren't required to carry it on themselves.
Your personal auto policy will deny any claim involving business use. A commercial auto policy covers your truck for business purposes, including liability while parked at a job site.
GL won't cover the $8,000 in tools stolen out of your truck overnight. An inland marine (tool floater) policy will. If your truck contents are worth more than $5K, this is a cheap policy that pays for itself the first time a job site gets hit.
For higher-end residential or commercial work, an umbrella policy sits on top of GL and provides additional limits for catastrophic claims. Often required by contract on commercial projects with higher coverage thresholds.
GL typically runs $50-150/month for a small residential operation, more for higher-risk trades. Workers' comp varies wildly — 1% to 30% of payroll depending on trade. Get a broker who specializes in contractors.
Usually no, since you're the only worker. State rules vary. Once you hire your first W-2 employee, almost every state requires it.