Handling a loved one’s estate isn’t just paperwork—it’s emotions, relationships, timing, and sometimes, family drama. Estate attorney Haley Rohrbaugh joins me to break down the REAL challenges families face, the mistakes that quietly cost thousands, and the simple planning steps that save families years of stress.

Haley brings 20+ years of experience in estate law, bankruptcy, and mediation—and she doesn’t sugarcoat what actually happens inside families when someone passes.

Key Discussion Points

• 00:00 – Why families struggle with estate administration
• 01:52 – The #1 source of estate drama (and how to prevent it)
• 03:34 – Why executors fight over the role — even when it’s a ton of work
• 05:18 – When Medicaid wipes out an estate
• 06:38 – What smart pre-planning actually looks like
• 07:11 – The “nervous gift” approach to avoid disputes
• 08:06 – Why working with an attorney early saves money
• 09:21 – What happens when family takes items too soon
• 11:40 – Sentimental items vs. taxable assets
• 13:06 – What REALLY needs to be valued in an estate
• 14:13 – When multiple family members want the same property
• 15:17 – How LLCs help families keep properties together
• 16:35 – Estate attorneys as mediators
• 17:21 – Haley’s path from Carrabba’s to estate law
• 19:19 – Growing up between PA and Florida
• 21:27 – How she met her husband through law
• 23:01 – Life as a working mom balancing a demanding legal career
• 26:38 – How we originally connected
• 29:10 – Haley’s top tips for avoiding costly mistakes
• 30:04 – Why every adult needs a power of attorney
• 32:01 – Why 18-year-olds should have basic estate documents
• 33:56 – Make pre-planning fun: the “jewelry party” method
• 36:02 – Why she once drafted a Viking funeral into a will
• 37:14 – Hiring professionals vs. family DIY
• 38:43 – Estate planning events & resources
• 41:48 – How to get started with Haley
• 43:22 – How often to update your documents

If you’ve ever wondered when to start planning, how to avoid family conflict, or what really matters in an estate, this conversation will be eye-opening.

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