Real Estate Consultant · Denver, CO · Member since 2026 · 38 posts · 8 votes
Another pattern I see on small land and infill deals is risk showing up not in the zoning itself, but in how the contract is structured relative to the entitlement path. On paper, the deal looks reasonable. In practice, a few things tend to cause problems later:
* Earnest money going hard before the true approval path is clear
* Entitlement periods that don’t align with realistic review timelines
* Assumptions that discretionary steps will be “routine” or fast
* Pricing anchored to a future unit count that hasn’t been de-risked yet
None of these automatically make a deal bad. But they do shift where the risk sits—and who’s actually carrying it. What often gets overlooked is that entitlement uncertainty isn’t just a technical issue; it’s a timing and capital allocation issue. Once money goes hard or expectations are set, flexibility drops quickly.
In my experience, aligning contract structure with entitlement reality early tends to preserve optionality and makes later decisions much easier, whether the outcome is moving forward, renegotiating, or walking away.
Curious how others here are thinking about contract timing and risk allocation on smaller land or infill deals.
@Jay Hinrichs Completely agree — risk is inherent, and the upside only exists because it’s not de-risked from day one.
What you’re describing is a good example of being intentional about where the risk sits. In some cases it makes sense to take it early; in others, it makes more sense to let approvals, engineering, or appeals play out and pay for certainty later.
Where I tend to see problems is less about taking risk, and more about taking it without realizing how much is being taken, or before the deal structure actually supports it. Once that’s clear, the decision to lean in or wait tends to be much cleaner.
@Jay Hinrichs Completely agree — risk is inherent, and the upside only exists because it’s not de-risked from day one.
What you’re describing is a good example of being intentional about where the risk sits. In some cases it makes sense to take it early; in others, it makes more sense to let approvals, engineering, or appeals play out and pay for certainty later.
Where I tend to see problems is less about taking risk, and more about taking it without realizing how much is being taken, or before the deal structure actually supports it. Once that’s clear, the decision to lean in or wait tends to be much cleaner.
comes down to location and jurisdiction.. if your an expert in a certain local and jurisdiction you can take more risks.. if you are new to this or dont know how the city operates you want to take less risk.
for me if I am looking at a deal in an area I dont know or have ever developed in I will hire a Good Civil and pay for a due diligence package based on their experience in the market place this is usually 5 to 10k . And 90% of the time the deal does not work and the 5 to 10k is just cost of doing business.. better to spend that money than a year of your life and 100k only to get turned down or have to severely modify your plans. This is why there needs to be big pay days Not small pay days like a rental or a 50k profit on a house flip..
PS I used to have a RE agent that worked for me with the same last name as yours its not a common name at least in my experience
@Jay Hinrichs That all tracks. Local knowledge materially changes how much uncertainty you can tolerate, and experienced operators absolutely earn the right to take more risk in jurisdictions they know well.
I’d agree that spending real money early—whether on civil, DD packages, or other upfront work—is often the cheapest way to find out a deal doesn’t work. Where I tend to see issues is less with whether money gets spent, and more with when and in what proportion, especially on smaller infill deals where the margin for error is tighter.
The common thread across both approaches is being honest about uncertainty early and aligning spend, timing, and expectations accordingly. That clarity is what ultimately preserves time, capital, and sanity.
And small world on the last name — definitely not one you hear every day.
@Jay Hinrichs That all tracks. Local knowledge materially changes how much uncertainty you can tolerate, and experienced operators absolutely earn the right to take more risk in jurisdictions they know well.
I’d agree that spending real money early—whether on civil, DD packages, or other upfront work—is often the cheapest way to find out a deal doesn’t work. Where I tend to see issues is less with whether money gets spent, and more with when and in what proportion, especially on smaller infill deals where the margin for error is tighter.
The common thread across both approaches is being honest about uncertainty early and aligning spend, timing, and expectations accordingly. That clarity is what ultimately preserves time, capital, and sanity.
And small world on the last name — definitely not one you hear every day.
out west here most of our jurisdictions have pre app meetings they run 1k to 2k and the city will get all the staff in and go around the table talking about issues that may come up.. some cities its mandatory first step..
That’s a good point, and it highlights how much process varies by jurisdiction. In places where pre-apps are formalized or mandatory, they can be a very efficient way to surface issues early and get alignment across departments.
Regardless of the specific mechanism—pre-apps, early civil work, or other upfront diligence—the common thread is using early clarity to decide how much risk to take and when. Once that’s clear, the rest tends to follow more cleanly
@Greg Saia as a land broker who always has to deal with sellers who have never heard of anything other than a 30 day escrow, and developers who would love to have a free, three year option to entitle/permit (especially since it CA it can take 9 mos-to-18 mos to get an approved Tentative Tract Map with Conditions Of Approval, plus another 6 mos-to-9mos+ to get to permit-ready) I do my best to massage sellers into understanding that their property has the most premium if they allow the buyer to mitigate risk. Of course, the premium for the extended escrow has to actually be there. With that said, we ask for non refundable deposits along the way to make sure the buyer stays focused on our deal and not allow it to be the one that continually falls to the bottom of the stack every time their dog gets sick, because I was able to help get them so much time. Also, the older and more successful a developer/builder is, the more they want as perfect/comfortable as possible timeframes, which when they can find a seller who is willing give that, great, I don't blame them, but those are also the guys who are on vacation every other weeks it seems like, and have a sense of entitlement to be honest, and love to grind sellers. I'd say my favorite builder-buyers that I work with currently are the ones who are kind of a hybrid on timing...I work to get them a healthy due diligence period of 60-90 days (maybe even an extension on top of that, if they show us what they've discovered so far, and what their remaining DD items are) so that they can truly assess the various potential constraints, budgeting, etc and then they close a month or two after that, and maybe even have a couple of addtl extensions built in (with addtl deposits). Those guys really know their stuff and by month six or so, they have things pretty figured out despite still having runway until they are actually approved and breaking ground. Also, many of them are using their own capital, so they are less IRR-driven than the builders whose margins thin out quickly if they have the cost of capital eating away while they work on entitlements/permits.
@Bryant BrislinThat’s a great breakdown, and it highlights how much of this comes down to incentive alignment, not just timelines.
What you’re describing with staged deposits, defined diligence periods, and accountability along the way is often what separates deals that move forward from ones that just linger. Time alone doesn’t mitigate risk, focused time with consequences does.
I also agree that capital source and experience level materially affect behavior. Buyers who are close to the risk tend to engage earlier and more decisively, whereas longer runway without structure can actually slow clarity.
At the end of the day, the most workable deals seem to be the ones where sellers get confidence the buyer is serious, and buyers get enough early clarity to make real decisions — even if full approvals are still a way out.