Real Estate Financial Planner™

Last chance to download the spreadsheet (free, before I delete it)

James Orr — Fri, 01 May 2026 00:05:04 GMT

This is the end of an era.

For years, The World’s Greatest Real Estate Deal Analysis Spreadsheet™ was the most thorough deal analysis tool an individual investor could get their hands on. Hundreds of calculations. Dashboard. Overrides. Multi-year projections. Proprietary calculations no one else has. Doing the corrections correctly… that no other spreads…

Some rate buydowns are bargains. Some are rip-offs.

James Orr — Wed, 29 Apr 2026 19:46:21 GMT

Buying down your mortgage rate is one of those line items on the closing disclosure that everybody glances at and almost nobody runs the math on.

And the math matters — because rate buydowns are full of inefficiencies. Some of them are absolute bargains: pay a little, save a lot over the time you actually plan to hold the property. Others are quiet rip-o…

The 3% mortgage you can buy without qualifying

James Orr — Tue, 28 Apr 2026 20:05:26 GMT

For a long stretch, money was nearly free. Buyers locked in 3% and 4% mortgages and stopped thinking about them.

Then rates climbed. New buyers face 7%+ on the same houses — and the math on a lot of deals just stops working at that rate.

But the old loans are still sitting there. And in the right deal, with the right paperwork, you can take one over inste…

I'm not a tax expert — so I built the tool I wish I had

James Orr — Mon, 27 Apr 2026 23:26:25 GMT

I am in no way a tax expert.

But sometimes the best apps come out of building the tool you yourself wished you had — the one you keep reaching for and never quite finding. So I built one for myself, to better understand and actually utilize the tax benefits that come with real estate investing. And now you get it too.

The new app is Real Estate Tax Estima…

44°, light rain, and a new app for your next flip

James Orr — Sun, 26 Apr 2026 20:07:27 GMT

It is 44° and lightly raining in Loveland, Colorado this afternoon — a much cooler day than we’ve had in a while — and I’m about to spend a solid hour in the hot tub with my kindle reading. But I wanted to get this one out to you first.

Every hard money lender quotes their deal differently. One leads with the rate, one leads with the points, one buries t…

What does enough actually look like for you?

James Orr — Sat, 25 Apr 2026 20:33:49 GMT

Heading to Denver tonight for dinner and a show with family, so I’ll keep this one short.

I built a new app this week: Real Estate Goal Planner.

Most of us know we want financial freedom from rentals. Far fewer of us have ever sat down and done the actual math — how many properties, throwing off how much cash flow, by what year, to cover what monthly numb…

79 ways to be 1% better at renting a property.

James Orr — Thu, 23 Apr 2026 14:03:46 GMT

I bought the Atomic Habits Workbook last week.

I’ve been obsessed with James Clear’s one idea for a while now — the one about getting one percent better at something every day. Not ten percent. Not five. One. The math is almost embarrassing: 1% compounded 365 times is 37× better in a year. And the reverse works too. 1% worse, every day, compounds down to…

I used to pray for Section 8 tenants.

James Orr — Wed, 22 Apr 2026 14:02:31 GMT

Back when I managed my own rentals directly — tenants calling me, me writing the checks, me at my home-office desk on the 5th of the month wondering who paid and who did not — I used to love Section 8 tenants.

Because the rent just… showed up.

The Housing Authority’s portion hits regularly. Every single month. No chasing, no late fees, no “I get paid Frid…

The sun damaging my face is filling Airbnbs.

James Orr — Tue, 21 Apr 2026 21:57:23 GMT

Yesterday I came home from the dermatologist with a dime-sized blister on my face.

It is a follow-up from the skin cancer they removed in November after I got back from Puerto Rico — and this visit the doctor spotted another precancerous patch on my high cheek/temple and zapped it on the spot with liquid nitrogen. Stay out of the sun, he told me.

Hat, lon…

I spent my first years chasing the wrong number.

James Orr — Mon, 20 Apr 2026 17:57:11 GMT

When I first started investing in rentals, the only number I cared about was cash-on-cash.

If it was double-digit, the deal was great. If it was not, pass. That was the filter — the whole filter. And because the market I lived in did not produce double-digit cash-on-cash at any reasonable leverage, I went shopping elsewhere. Cheaper markets, lower price …

My best rentals are quietly becoming my worst.

James Orr — Sun, 19 Apr 2026 18:55:12 GMT

The longer I hold a rental property, the lower my return on equity gets.

That sounds backwards until you watch it happen. The rent goes up. The mortgage gets paid down. The property appreciates. Everything is working — and yet the return on the equity trapped inside that deal quietly falls every year. More equity, same-ish cash flow, same-ish appreciatio…

The Navy had an SOP for everything. Your next flip probably doesn't.

James Orr — Sat, 18 Apr 2026 14:59:24 GMT

When I got certified to operate nuclear reactors for the United States Navy, there was a standard operating procedure for almost everything.

That is exactly what you would expect. You do not improvise on a nuclear reactor. You do the step, you check the step, you document the step, and you move to the next one — because the cost of a missed step is measu…

It's Thursday. My checklist for tonight has one item.

James Orr — Thu, 16 Apr 2026 22:41:05 GMT

It’s Thursday, and that means one thing in my house: Love is Blind watch party.

I’ve got company coming over, I’ve got more snacks than we could possible eat tonight, and I’ve got opinions about who should not have said yes. The checklist for tonight is short: couch, bean bag chairs, Matthias in my lap, remote, volume up.

The checklist for managing a rent…

It's Tax Day. Here's how to not pay all of it at once.

James Orr — Thu, 16 Apr 2026 01:29:22 GMT

My CPA finished my taxes weeks ago.

If you sold a rental this year the traditional way — cash sale, 1099-S, capital gains due in full — you already know what the check feels like. You recapture every dollar of depreciation you ever took, you pay long-term capital gains on the rest, and the whole bill lands in a single April.

There’s another way, and it’s …

The DMV and your mortgage lender have way too much in common

James Orr — Wed, 15 Apr 2026 01:04:53 GMT

I had breakfast with Tammy this morning, and then this afternoon I drove over to the DMV to renew my driver’s license.

We’ve got some travel booked later in the year, and my license expires before we go. So rather than find out at a TSA checkpoint that my ID is no good, I figured I’d get it handled now — before I get turned away at the airport.

You know t…

My stock broker tracks every penny — why can't my rental portfolio?

James Orr — Mon, 13 Apr 2026 14:03:49 GMT

I’m spending this morning managing my stock investments.

I’ll pull up my brokerage account, and within about ten seconds I can see every trade I’ve made this year, my realized and unrealized gains, dividends received, and a complete breakdown by sector. If I want a tax report, there’s a button for that. If I want to export everything to a CSV for my acco…

Four app updates before the tortellinis hit the table

James Orr — Sun, 12 Apr 2026 20:56:54 GMT

A friend is coming over tonight for tasty cheese tortellinis. We’ll probably end up out on the deck overlooking the mountains, and then settle in for a couple episodes of the latest season of Love is Blind — because apparently that’s what passes for a Saturday night around here and I’m not mad about it.

But before dinner starts, I wanted to get these fou…

Two new apps before we hit the next Mando episode

James Orr — Sat, 11 Apr 2026 23:47:37 GMT

Tammy and I are getting ready for The Mandalorian and Grogu this summer, so we finally started working through The Mandalorian series. A few more episodes are queued up for tonight, but I wanted to ship these two apps before we hit play.

Both are live as of today.

Repair or Replace Decision Tool

The cost-per-year math you should be doing on every roof, HVA…

Two new apps before The Bear starts

James Orr — Fri, 10 Apr 2026 21:54:00 GMT

Friday night plan: a few friends coming over, pizza on the way, and another stack of episodes of The Bear queued up. I wanted to ship two new apps before they show up at the door.

Both are live as of today.

Wholesale Deal Analyzer

The MAO calculator I wish every wholesaler had open before they pick up the phone:

Auto-calculates Maximum Allowable Offer using…

Why the 5% maintenance rule will eventually break you

James Orr — Thu, 09 Apr 2026 23:52:14 GMT

There’s a rule of thumb you’ll hear in every real estate podcast, every BiggerPockets thread, every spreadsheet template you download: set aside X% of rent for maintenance, another Y–Z% for capex.

It’s clean. It’s memorable. It’s wrong. Regardless of what numbers they give you.

Here’s why. Imagine two single-family rentals on the same street. Both rent fo…