Understand your options before you decide anything.
These guides, articles, and tools are written for investors making real decisions — not to generate leads. Read them before your next conversation with any adviser. If you have questions after, we're happy to talk.
Not Sure Where to Start?
Choose the path that best matches your situation.
Retiring From Landlording
For rental property owners evaluating whether to sell, exchange, or transition to passive ownership.
Start Here →Considering a 1031 Exchange
For investors evaluating tax deferral options before selling appreciated real estate.
Start Here →Exploring Delaware Statutory Trusts
For investors interested in passive real estate ownership through a 1031 exchange.
Start Here →Selling Farmland
For farm and land owners evaluating transition, tax planning, and passive ownership options.
Start Here →Business Owners With Real Estate
For business owners evaluating the tax and planning implications of selling both a business and associated real estate.
Start Here →Plain-language guides for investors
Written for investors facing real decisions. Read them before your next conversation with any adviser.
The Retiring Landlord's Playbook
A plain-language guide to your options when selling rental property — capital gains taxes, 1031 exchange rules, DST basics, and how to think through the decision before signing anything.
Farmland Transition Planning Guide
Selling farmland involves different considerations than other real estate. Tax implications, family dynamics, estate planning, and passive income options for farm families navigating a transition.
Business Exit & Real Estate Planning
When a business sale includes real estate, the structure of the transaction can significantly affect the tax outcome on the real property. Options available to business owners before they sign anything.
These guides are for general educational purposes only and do not constitute investment, tax, or legal advice. Consult your CPA and legal counsel before making any decisions.
In-depth resources on key topics
Each hub page covers a topic in depth — with plain-language explanations, comparison tables, FAQs, and honest discussion of when a strategy may not be the right fit.
1031 Exchange Rules, Deadlines & How It Works
A comprehensive guide to 1031 exchanges — how they work, what the IRS requires, the four exchange types, and when an exchange may or may not make sense for your situation.
- 45-day and 180-day deadline rules
- Qualified intermediary requirements
- Boot, debt replacement, and partial exchanges
- When a 1031 exchange may not make sense
- How DSTs fit as replacement property
Delaware Statutory Trust (DST) Investments Explained
A plain-language guide to DST investments — how they work, who they may be appropriate for, what the risks are, and how to evaluate a specific offering before committing capital.
- DST structure and how investors participate
- Common property types inside DSTs
- Full risk disclosure — illiquidity, sponsor risk, distributions
- DST due diligence checklist
- DST vs. direct real estate ownership
Retiring From Landlording — Your Options Explained
Written specifically for landlords who are ready to exit active management. Covers tenant fatigue, the tax surprise, the three paths forward, and how to evaluate them honestly.
- Capital gains, depreciation recapture, and NIIT
- Sell outright vs. 1031 vs. DST — compared honestly
- The 45-day identification window under time pressure
- Estate planning considerations for rental property
- How Insight works with retiring landlords
The Retiring Real Estate Investor
A podcast for real estate investors approaching a major transition — evaluating a sale, exploring 1031 exchanges, or thinking through what comes next. Hosted by Insight Investment Advisers.
Future episodes will explore 1031 exchanges, Delaware Statutory Trusts, tax planning considerations, farmland transitions, and real estate exit strategies for investors navigating significant decisions.
- How a 1031 exchange actually works — step by step
- What landlords get wrong about their tax exposure
- Farmland transitions — the financial and family dimensions
- DSTs explained — benefits, risks, and what to ask before investing
- When a 1031 exchange doesn't make sense
- Estate planning for real estate investors
The Retiring Real Estate Investor Podcast
Coming Soon
Episodes will cover 1031 exchanges, Delaware Statutory Trusts, tax planning considerations, farmland transitions, and real estate exit strategies.
Browse by investor type
Find content relevant to your situation. Each link goes to a section of the site that covers that topic in depth.
