A Holiday Wish List for Smarter Homeownership

All we want for the holidays is… a lower monthly housing payment, less taxes, a bigger house, and did I say less taxes???

As we wrap up a year defined by high interest rates, a national housing crisis filled with unaffordability, and tight home inventory, I wanted to take the time to showcase some of the best companies that help home buyers and current homeowners.

Homeownership comes with having difficult conversations, and this resource guide should help you talk through those difficult conversations with your loved ones.

Some of this information could help you save money, even if you are already a homeowner!

The “Smart Buy” Department

Tools to help you afford the home you want.

1. Jubilee

The Gift: A lower down payment (by separating the land). In expensive markets, the dirt costs more than the house. Jubilee solves this by buying the land, so you only have to buy the house. You pay a monthly ground lease for the lot, which drastically reduces your upfront down payment. You can always buy the land later if you want to.

Why it’s on the list: It lowers the barrier to entry for prime neighborhoods. Instead of having to sell equities and pay capital gains, you get to buy a home with a much much lower down payment.

2. CoBuy

The Gift: Buying with friends, without the drama. Joint ownership is on the rise, but it can be legally messy. CoBuy acts as the “operating system” for co-ownership. It handles the structuring, agreements, and exit strategies for friends, unmarried partners, or multi-generational families buying together.

Why it’s on the list: It fixes the “roommate” economy, allowing you to pool resources to afford a better home while protecting your relationships.

I’m proud to have earned a CoBuy-certified™ Pro credential!

3. Pacaso

The Gift: A luxury second home for 1/8th the price. Dreaming of a holiday getaway? Pacaso allows you to buy a “share” (1/8th to 1/2) of a luxury vacation home. Unlike a timeshare, this is true real estate ownership that you can sell later. They handle the interior design, property management, and scheduling.

Why it’s on the list: It democratizes luxury. You get a $4 million Aspen lodge for a fraction of the cost, and you split the operating expenses with other owners. This is especially helpful for those who want to diversify their investments without dealing with the typical headaches of home ownership. This also helps you enter other markets, such as Europe, that you typically wouldn’t think about buying.

🛠️ The “Fix & Maintain” Crew

Services that stop your house from becoming a money pit.

4. Remi

The Gift: A roof purchase that doesn’t feel like a robbery. Roofing is notorious for “change orders” and opaque pricing. Remi, a Y Combinator-funded startup, offers a managed marketplace for roofing. They analyze your roof and give you a guaranteed price.

Why it’s on the list: They vet the contractors and hold the liability. Plus, if you have solar panels, they handle the complex “detach and reset” process that most roofers refuse to touch.

5. Frontdoor

The Gift: A plumber in your pocket. Before you pay a $150 “trip charge” for a contractor to flip a breaker switch, try Frontdoor. Their app connects you to licensed tradespeople via video chat to diagnose and fix problems yourself.

Why it’s on the list: The first chat is free! Their membership (unlimited video calls) costs less than a single contractor visit. It’s telemedicine for your house.

6. Armadillo

The Gift: A home warranty that actually works. Traditional home warranties are famous for denying claims. Armadillo positions itself as a “home health subscription.” They have removed the “pre-existing condition” clauses and offer higher coverage limits for modern appliances.

Why it’s on the list: It allows you to use your own contractor (unlike legacy warranties) and provides a modern approach to home warranties.

7. Inspectify

The Gift: A home inspection that generates actionable data, not just a dusty PDF with no pictures. Finding and scheduling a reliable inspector is usually a headache of phone tag and varying quality. Inspectify streamlines the booking process and utilizes proprietary software to deliver standardized, data-driven reports.

Why it’s on the list: The platform can instantly translate inspection findings into repair cost estimates, helping you negotiate faster and budget for renovations with actual numbers rather than guesses. They also include a home warranty in select markets that is connected to the inspection at no extra cost to you

💸 The “Cash & Value” Unlocks

Ways to find money in the home you already own.

8. Ownwell

The Gift: A lower tax bill, on autopilot. Property taxes often rise, and homeowners don’t have the time to figure out how to lower property taxes. Ownwell uses AI to identify over-assessments and files an appeal with the county on your behalf.

Why it’s on the list: It is purely success-based. They only charge you money if they will save you money, and without upfront costs.

9. Remoov

The Gift: Cash for your clutter. Moving or downsizing? Remoov picks up everything you don’t want. They sell what they can, donate what they can’t (for the tax write-off), and recycle the rest. You get 50% of the resale value.

Why it’s on the list: It turns a stress/cost center (junk removal) into a potential profit center, while keeping items out of the landfill.

10. Revive Real Estate

The Gift: Flipping your own house before you sell. Selling “as-is” leaves money on the table. Revive fronts the capital and manages the contractors to renovate your home before you list it. You pay them back from the sale proceeds.

Why it’s on the list: Homeowners keep the upside profit from the renovation without dipping into their savings or taking out a high-interest loan.

11. Deferred

The Gift: It’s common for intermediaries to hold your money in an interest-bearing account and retain the interest earned on your funds when doing a 1031 exchange. Deferred shares the interest earned on your funds, and a share of that interest covers their fee.

Why it’s on the list: Investors who are taking advantage of a 1031 exchange transfer can save hundreds, if not thousands of dollars, from not having to pay a company to handle the 1031 exchange.

12. Rhino

The Gift: Rhino helps homeowners find insurance for wildfire-exposed homes without the usual runaround. Rhino tells you what’s hurting your insurability and how to fix it — then points you to carriers who will actually quote you. If you’ve been non-renewed, declined, or have increasing premiums due to wildfire risk, we’d love to meet you.

Why it’s on the list: It takes one of the biggest homeowner pain points in California and makes it simple, fast, and way less intimidating.

🛡️ The Protection & Agency

The final pieces of the modern housing stack.

13. Trust and Will

The Gift: Making the process of writing your Will, setting up your Trust, or settling a loved one's estate as simple and straightforward as possible

Why it’s on the list: Their prices are competitive, and they also have a network of attorneys that can assist in case of specific concerns.

14. ContextRE

The Gift: A real estate brokerage that offers context. Instead of arbitrarily charging a specific fee, ContextRE offers a flexible menu that allows you to actually negotiate the commission that you pay during the process of buying, selling, or renting a home. You are also working with a company that can help you in multiple states and countries without having to pay extra referral fees (partially the reason commissions are inflated). Every other company provides an offering that doesn’t let you pick the type of services you need, and with horrible customer service — I know this because I’ve been there!

Why it’s on the list: contextRE unbundles the real estate agent. Pay a flat fee, a percentage, or even hire them by the hour for specific consulting tasks.

Happy Holidays and Smart Housing!

Disclosure: With some of these companies, I have secured discounts for you. Separately, they may offer a referral reward to me as well. I do not recommend companies simply based on referrals. I recommend companies based on the fact that they offer a product that can save you hundreds, if not thousands of dollars. I always advise you to look into other companies, so that you can compare and contrast.