Upcoming Event · August 22, 2026
Senior Real Estate Planning

Plan the Transition
Before It Plans You

A two-hour planning session for Lamorinda families navigating senior real estate decisions: what to do now, what can wait, and how to avoid the mistakes families make when they wait too long.

Ben hosts occasional workshops for Lamorinda homeowners and their families. Add your name to the list.

Reserve Your Spot Join the Interest List

Date

August 22, 2026

Location

Moraga Country Club

Format

2 hours · Presentation · Q&A

Presented By

Ben Olsen, REALTOR with BrightWork Realty Advocates

Ben Olsen

REALTOR, BrightWork Realty Advocates

Ben has worked exclusively with Lamorinda homeowners for more than a decade. He built BrightWork Realty Advocates around one idea: that families navigating a senior real estate decision deserve a process, not a pitch. These workshops are how that starts.

Jennifer Raftis, Certified Professional Organizer and founder of Efficiency Matters

Jennifer Raftis, CPO

Certified Professional Organizer

Efficiency Matters, LLC

Jennifer is a Certified Professional Organizer specializing in senior transitions and downsizing. She helps families work through decades of belongings in a way that is methodical, respectful, and actually finishable. She brings the logistics that most real estate conversations leave out.

Efficiency Matters →

Who This Is For

Two audiences, one shared conversation

If You Own the Home

You've probably thought about what comes next, downsizing, renting, staying put, without having a clear plan. This workshop is for homeowners who want to understand their options while they still have all of them.

  • You've owned the home a long time and aren't sure what selling would mean financially
  • You're thinking about moving closer to family but haven't run the numbers
  • You want to know what the house could do for you in retirement

If Your Parents Own the Home

Adult children often see the situation more clearly than their parents do: the deferred maintenance, the safety concerns, the equity sitting idle. This workshop helps you have that conversation with a shared framework instead of starting from scratch.

  • You've been wondering how to bring this up without making it a difficult conversation
  • You want to understand the financial picture before any decisions get made
  • You're worried about what happens if there's no plan in place

Workshop Agenda

What Happens in Two Hours

The Legacy Home Question

What role should the family home play in the next chapter, and in the estate? Ben walks through the real options: stay, downsize, rent, sell, and what each path actually costs and creates.

What to Do Now vs. What Can Wait

Not everything needs to happen at once. Ben maps out what families should address immediately (estate documents, tax planning conversations, basic safety) and what can be structured over a 12-24 month horizon.

The Part Nobody Plans For

Forty years of belongings is not a weekend project, and it is the reason most families stall out before they start. Jennifer Raftis walks through how a downsizing move actually works: what to sort first, what to do with the things nobody in the family wants, and how to sequence the work so the house is ready when the plan is. Families who handle this well get to make decisions on their own timeline instead of under pressure.

Taxes, Trusts, and Probate, In Plain English

Ben isn't an attorney or a CPA. But he knows what questions to ask and what gets families in trouble when they don't ask them. The workshop gives you the vocabulary and the questions, so the conversation with your own CPA and estate attorney starts further down the road. Any strategy involving a significant gain should be reviewed with your CPA and estate attorney before you decide.

Trusts, titling, and probate. Outdated documents and improper titling can turn a clean transition into a probate nightmare. The workshop covers the questions to bring to your estate attorney, not the legal answers.

Keep it as a rental. A home with a low Prop 13 basis and strong rental demand may generate more long-term family wealth as a held asset than as a sale. Ben helps families model both scenarios honestly, including the one that does not result in a listing.

1031 exchange. Sell the property and reinvest the proceeds into another qualifying property, deferring the capital gains tax event. You move the equity forward instead of settling the tax bill at closing.

Delaware Statutory Trust. A 1031-eligible vehicle that lets you invest those proceeds into a professionally managed real estate portfolio without taking on property management yourself. Useful when you want the tax deferral but not a new landlord role.

Installment sale. Spread the recognition of gain over time instead of taking the full tax hit at closing. Whether it fits your situation is a question for your CPA, but many families have never heard it raised at all.

Step-up in basis. When a property transfers to heirs rather than selling during your lifetime, the cost basis resets to current market value, potentially eliminating the embedded gain entirely. Worth understanding before making any irreversible decision.

Ben knows how to bring these questions into the conversation alongside your CPA and estate attorney.

Practical Next Steps for Your Specific Situation

Every family leaves with a list of concrete actions, not just information. For some families that's "call your estate attorney." For others it's "get a planning-oriented home valuation." The workshop ends with clarity, not more questions.

Most families wait until a crisis forces the conversation. The families that plan ahead have more options, less friction, and better outcomes. Ben started hosting these workshops because the information that helps people plan well just isn't easy to find, and most agents aren't interested in having a conversation that doesn't end with a listing agreement.

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Common Questions

Workshop Questions, Answered

What is the BrightWork senior real estate planning workshop?

A two-hour educational session for Lamorinda homeowners and their adult children navigating senior real estate decisions. Ben Olsen leads the session, joined by Jennifer Raftis, a Certified Professional Organizer who specializes in senior downsizing and move management. Topics include the legacy home decision, what to do now vs. later, tax and estate basics, and practical next steps.

Who should attend the senior real estate planning workshop?

The workshop is designed for two groups: seniors and homeowners who are thinking about their next chapter, and adult children who are helping their parents plan a transition. Both audiences leave with a clearer picture of options, tradeoffs, and what to do next.

Is the workshop free?

Yes. There is no cost to attend and no obligation to work with BrightWork or list a property.

What does the workshop cover?

The workshop covers four main topics: the legacy home decision (stay, downsize, rent, or sell), a now-vs-later planning roadmap, plain-language tax and estate context, and concrete next steps for each family's specific situation.

Does the workshop cover options for avoiding capital gains on a home sale?

Yes. One session covers strategies including 1031 exchanges, Delaware Statutory Trusts, installment sales, and the step-up in basis that applies to inherited property. The goal is to give families the vocabulary and questions to bring to their CPA and estate attorney, not to provide tax advice. Knowing the options exist is the starting point.

What is a Delaware Statutory Trust in real estate?

A Delaware Statutory Trust, or DST, is a passive real estate investment vehicle that qualifies as a 1031 exchange replacement property. It allows a seller to defer capital gains taxes by reinvesting sale proceeds without acquiring and managing another physical property. It is commonly used by sellers who want the tax deferral of a 1031 exchange but do not want the responsibility of being a landlord. DSTs require coordination with a qualified intermediary, a financial advisor, a CPA, and an estate attorney.

Why BrightWork

The Smart Way to Real Estate

01

Superior Presentation

Professional photography, floor plans, 3D tours, and Sky Tours on every listing. Not the luxury package. The baseline.

02

Premium Portal Presence

Zillow Showcase and premium homes.com membership. Higher view counts, better placement, and buyer inquiries that route to your listing team.

03

Integrated Campaigns

Every sign, mailer, and open house connects to a digital system. Curious neighbors become trackable leads.

04

Modern Offer Management

Real-time portal data guides pricing decisions. Final Offer platform for properties with strong multi-offer potential.

05

Financial Tools & Capital Programs

Capital to fund pre-sale improvements with no out-of-pocket cost until close. Plus programs that remove the timing trap entirely.

BrightFlip (Pre-Sale Improvements) Buy Before You Sell
06

Off-Market Strategy

A private list of serious Bay Area buyers. Test demand quietly or gain early access before properties hit MLS.

Off-Market Access (Buyers) Quiet Listing (Sellers)
07

Advocacy for Unsold Homes

When a home hasn't sold, we don't re-list at a lower price. We conduct a forensic review and relaunch with a rebuilt strategy.

08

Built to Close Clean

Pre-sale prep, real fixes, and full disclosure to every buyer before the house lists. He structures listings to attract the best first offers from a position no one can argue with. The preparation is the negotiation.