I've lived in Ventura for 20 years and work in real estate here, and I've been spending quite a bit of time looking at the short-term vacation rental market now that Ventura's STVR moratorium has been lifted. I think there is a really interesting opportunity here, but it's also a market where you can get yourself into trouble pretty quickly if you buy the real estate first and figure out the STVR side afterward. There are really two different stories happening in Ventura right now. Pierpont is at its STVR permit limit, so new applicants are on a waitlist. Midtown, on the other hand, currently has room under its 100-STVR limit. Those are two very different investment opportunities, and I think investors need to understand that distinction before they start shopping for properties.

Pierpont is the scarcity play

Pierpont is probably the first place most people think about when they hear "Ventura vacation rental." You're close to the beach, you can walk or bike to the water, there is a real vacation feel, and there are a limited number of properties. The problem is that you can't just buy a house in Pierpont and decide you're going to turn it into an STVR. The area has reached its permit cap, so new applicants go onto a waitlist. There is also one very important thing to understand if you're buying an existing STVR: the STVR permit does not transfer with the sale of the property. The new owner needs to obtain a new STVR permit. So I would not look at an existing STVR property and think, "I'm buying the permit." You're not. What makes the property interesting is the possibility of getting into a very constrained market where the number of permits is limited and there is already a waitlist.

That makes understanding the waitlist extremely important. If I were considering buying a Pierpont property specifically as an STVR, I'd want to understand exactly what the process is for a new owner, where the waitlist currently stands, how many people are ahead of me, how often permits become available, and what the realistic timeline might be.

There is also going to be turnover among existing Pierpont operators every year. Ventura's new program has significantly increased the cost of maintaining an STVR. The current permit fee is $1,526, with additional inspection and renewal costs, along with increased compliance requirements. For a property doing $150,000 a year in gross revenue, that probably isn't going to change the owner's decision. But think about the marginal operator. Maybe they're doing $40,000 or $50,000 a year, the house needs a lot of maintenance, insurance has gone up, they're paying a manager, and now they're dealing with increased permitting costs and compliance. At some point, some owners are going to decide it's not worth it anymore.

I don't think anyone should assume there will be massive turnover every year, but I do think it's something worth watching closely. The interesting question isn't whether the seller has an STVR permit, because that permit does not transfer. The question is whether a new owner has a realistic path to getting a new permit. That's a very different way of looking at the property.

Midtown is a completely different opportunity

Midtown is currently much more straightforward. The city has a 100-STVR limit there, and there is currently capacity available. That means an investor doesn't necessarily have to wait for an existing operator to leave the program. You can potentially find a property that meets the requirements, buy it, and apply for a new STVR permit while there is still capacity. So, very simply, Pierpont is the scarcity and waitlist opportunity, while Midtown is the opportunity to get in while permit capacity still exists. If I were looking today, I'd be looking at both. Pierpont is potentially the scarcity play, while Midtown is the opportunity to establish a new STVR without having to wait for an existing permit to become available. If Midtown starts filling up, that dynamic could change pretty quickly.

Don't start with Airbnb. Start with the City.

This is probably the biggest thing I'd tell somebody thinking about buying an STVR. Don't start by looking at Airbnb. Start by figuring out whether the property can actually operate as an STVR. Before I got serious about a property, I'd want to know whether it is in an eligible area, whether there is permit capacity, whether there is a waitlist if there isn't capacity, whether the property meets the parking requirements, whether there are HOA restrictions, whether there are zoning or building issues, whether there are code violations, and whether there is anything about the property that could prevent it from qualifying. The fact that you can see five Airbnbs on the same street doesn't mean the sixth house automatically qualifies. I would not wait until after closing to figure this stuff out. The STVR requirements need to be part of your acquisition due diligence from the beginning.

Then I'd start looking for the right property

Once I knew there was a realistic path to an STVR permit, then I'd start looking at the real estate. For Ventura, I'd put location way ahead of square footage. Beach proximity matters, walkability matters, outdoor space matters, parking matters, and being able to walk to coffee, restaurants and the beach matters. I'd much rather have a smaller, really attractive house in an incredible location than a huge house that doesn't have much going for it other than square footage. You have to look at the property through the eyes of somebody spending three or four nights there. Would I want to spend a weekend here? Would I bring my family here? Would I pay a premium to stay here instead of somewhere else? Does it photograph well? Is there a great outdoor area? Are the beds comfortable? Can six people actually sit around the dining table? Does the kitchen have everything somebody needs?

You're not just buying a house. You're creating a hospitality product.

Underwrite it conservatively

This is another place where I think investors can get themselves into trouble. I wouldn't take an Airbnb revenue estimate at face value. I'd look at comparable properties and try to figure out what they're actually doing. I'd want to understand nightly rates, occupancy, seasonality, length of stay and the type of property that's actually generating the revenue. Then I'd build my own model. Property taxes, insurance, management, utilities, landscaping, pool service if applicable, repairs, supplies, cleaning, platform fees, furniture replacement and everything else need to be accounted for. And don't forget the 10% Transient Occupancy Tax. Ventura currently requires a 10% TOT on qualifying stays, along with filing and payment requirements.

I'd run three scenarios: a conservative case, a realistic base case and an upside case. If the property only works if you're at extremely high occupancy and getting the top ADR in the market, I probably wouldn't buy it. I want the deal to work when things don't go perfectly.

Insurance is something I'd figure out before buying

I'd also get an STVR insurance quote before I removed contingencies. I wouldn't assume my normal homeowners policy covers what I'm doing. I'd want a policy specifically written for the way I'm going to use the property and understand the liability coverage, property coverage, guest damage, loss of rental income and any coastal, flood or earthquake exclusions that might matter. And I'd want the actual policy, not somebody telling me over the phone that I'm covered. The City requires appropriate rental insurance as part of the STVR program. This is one of those expenses that can materially change your numbers, so I would know the cost before buying.

The business license is another piece

There is also a City business license requirement. It's worth understanding that the business license and the STVR permit are not the same thing. Having a business license doesn't give you permission to operate an STVR. There are several pieces that need to come together before you can actually start renting, which is why I'd build the permitting process into the acquisition timeline rather than treating it as something I'll figure out after closing.

Then comes the fun part. making the house good

Furnishing is one area where I think you can either create a great rental or a mediocre one. I wouldn't necessarily spend a fortune, but I also wouldn't furnish a beach rental with whatever was left over from somebody's garage. The beds matter. The linens matter. The outdoor furniture matters. The kitchen matters. Lighting matters. Art and design matter. And everything needs to be durable because you're going to have a lot of people using it. I'd spend money on the things guests actually experience and try not to waste money on things that don't add anything to the stay.

I'd also have professional photography done. Your Airbnb listing is basically your storefront, and good photography can make a significant difference in how people perceive the property.

You need a handyman

This sounds like a small thing until you're dealing with a guest who can't get the front door open at 9:30 at night. Things break. A toilet runs, a garbage disposal dies, a refrigerator stops working, a lock fails, a window breaks or a pipe leaks. You need somebody local who can actually respond. Before I opened the property, I'd want a good handyman, plumber, electrician, HVAC guy, appliance repair person, locksmith, landscaper, cleaner and anybody else I might need. I'd also have backups for the important ones. The goal is to have those relationships before you have the emergency.

But honestly, the manager is probably the most important piece

If you ask me what I think is the single most important operational decision after buying the property, it's the manager, especially if you aren't living nearby. A great manager can make an average property perform very well. A bad manager can destroy a great property. The manager is dealing with the guest, coordinating the cleaner, handling the 11 PM phone call, dealing with the broken appliance, watching reviews, dealing with neighbors and making sure the property is actually ready when the next guest arrives.

And Ventura's rules make the local-response component particularly important. I'd interview managers before I bought the property. I'd ask who actually answers the phone, how many properties they manage, how quickly they can get somebody to the house, who cleans, who handles maintenance, what they charge, whether they mark up repairs, who owns the Airbnb account and what happens if I want to terminate the agreement. I'd also want references. The big management company with the nicest website isn't necessarily the best operator. I'd rather have a smaller local manager who is obsessive about the property than a company managing 100 rentals where mine is just another number.

Management can make or break the investment

Two investors can own nearly identical properties and have completely different results. One has a great manager who communicates quickly, keeps the house clean, prices it properly, handles maintenance immediately and keeps guests happy. The other has a manager who is slow to respond, misses maintenance issues and lets reviews deteriorate. Those properties may look identical on a spreadsheet. The financial results won't be. That's why I'd treat management as part of the underwriting. If I can't find a manager I trust, that would make me think twice about buying the property.

Negotiating the purchase is where this gets interesting

If I'm buying an STVR, I'm not just buying a house. I'm buying an investment with a particular income-producing use. So I'd want to know what the seller is actually basing their price on. If they tell me, "This property makes $150,000 a year," I'd want to see the actual history. What was the occupancy? What was the ADR? What were the expenses? How much went to management? How much went into repairs? What did they actually net? I'd also be looking very closely at the physical condition of the house. A property that looks great on Airbnb can have a roof that's 25 years old, old plumbing, electrical issues, drainage problems or a deck that's going to need $30,000 of work. All of that is part of my purchase price. My calculation is basically purchase price plus repairs plus furnishing plus startup costs equals my real basis. Then revenue minus all operating expenses equals actual NOI. That's the number I'm investing for.

I would also look for tired owners

This is where I think there could be an interesting off-market strategy in Ventura. Find existing STVR owners. Some are going to be excellent operators and have no interest in selling. Others are going to be tired. Maybe they're out of town, maybe they're getting older, maybe they're tired of dealing with guests, maybe their insurance went up, maybe the new permit costs aren't worth it to them, or maybe the property needs a lot of work. Those are the owners I'd want to talk to. I'm not necessarily trying to buy their "Airbnb business." I'm trying to find a good piece of Ventura real estate where I understand the property's STVR history and, most importantly, understand the actual process and likelihood of obtaining a new permit as the buyer.

Again, the seller's permit doesn't transfer. That needs to be crystal clear before I put a premium on the property.

The waitlist is something I'd watch very closely

If I were investing in Ventura STVRs, I'd track the Pierpont waitlist almost like I track inventory. I'd want to know how many people are waiting, how many permits are active, how many operators renew, how many drop out and how quickly the list moves.

I'd also want to understand why people are leaving. If the increased permit cost and compliance requirements cause marginal operators to leave, those openings could eventually create opportunities for people on the waitlist.

I wouldn't build a purchase decision around that assumption, but I'd absolutely watch it. The regulatory scarcity could become an important part of the Ventura STVR market.

Midtown could be the easier entry point

For someone starting from scratch, Midtown may currently offer a more straightforward path because there is capacity under the 100-STVR cap. That allows you to focus on finding a great property rather than waiting for a permit to become available.

If I were looking today, I'd probably have two separate acquisition strategies. For Midtown, I'd look for the best property that qualifies and get into the permit process while capacity exists. For Pierpont, I'd be watching the waitlist and talking to existing STVR owners and property owners who may eventually want out. Those are two very different strategies.

Don't ignore the neighbors

This is especially important in coastal neighborhoods. You're buying into a residential community, and your guests aren't necessarily going to behave like homeowners. You need to think about noise, parking, trash, outdoor gatherings, late-night arrivals, dogs, smoking and occupancy. A good manager should have systems in place to deal with those issues immediately. A bad operator can turn an entire neighborhood against STVRs, and that can eventually become a regulatory problem for everyone.

Look for multiple exit strategies

This is one of my biggest rules for any investment property: don't buy an STVR that only works as an STVR. Ask yourself what happens if the rules change again. Can I rent it long-term? Can I rent it mid-term? Would an owner occupant want it? Could I sell it without needing the STVR income to justify the price? If the answer to those questions is yes, I feel much better. The best investment has multiple exits. If the only reason the property is worth what you're paying is because it can generate STVR revenue, you're taking a much bigger regulatory risk.

What would I actually buy?

If I were looking today, I'd be looking for a property with a great location, good parking, outdoor space, a layout that works for families or groups, and enough character that it can stand out online. I'd want the numbers to work without heroic assumptions. I'd want an insurance quote before I got too far into the transaction. I'd want a manager lined up. I'd want my contractor and handyman network lined up. I'd want to understand the City's requirements. And I'd want a clear answer on the permit situation before I got too far down the road.

For Pierpont, I'd be watching the waitlist and looking for existing operators who may eventually want out. For Midtown, I'd be looking at the available permit capacity and trying to find the best property before that capacity disappears. I think that's the interesting part of Ventura right now. Pierpont has scarcity. Midtown has opportunity. The moratorium being lifted doesn't mean every property suddenly became an STVR opportunity. It means the market is open again, and investors who understand the regulations, the economics and the operational side have an opportunity to find the properties that actually make sense.

For me, the biggest takeaway is that an STVR investment is really three investments rolled into one: the real estate, the regulatory opportunity and the operating business. You need all three to work. And if I had to pick the one thing I would spend the most time on after finding the right property, it's the manager. A great property with a bad operator can be a bad investment. A great property with a great operator can be a very different story.

I'm curious what other investors are seeing. What are you seeing for actual ADR and occupancy? Are you self-managing or using a local manager? And if you've already gone through the new permitting process, what hurdles have you encountered?

I'd love to compare notes with other investors looking at the Ventura market.