“AI will not replace humans, but those who use AI will replace those who don't.” - Ginni Rometty

I’ll be honest — I didn’t think I needed an AI messaging assistant.

I only manage two properties, and guest messaging has never been a major pain point. I'm not juggling dozens of check-ins a week or running some massive operation. So when I first came across HostBuddy.ai, it seemed like overkill — a tool built for the property management companies or co-hosts with larger portfolios.

But here's the thing: even as a small-scale host, there's this constant mental weight.

You know what I'm talking about: checking for messages before bed, keeping one eye on your phone at all times, always being "on call" just in case someone can't figure out the door code at 11 PM.

Utilizing a free six-week trial, I figured why not give it a real test, especially with an international trip coming up where I'd be dealing with a completely different time zone.

When I consider adding any new technology into the fold, I want it to at least one of two things: save me time or save me money.

Here's what I learned in my initial experience with HostBuddy — and whether it's actually worth it for smaller hosts like us.

What Is HostBuddy.ai?

HostBuddy's main focus is automated guest messaging — actually understanding what guests are asking and responding intelligently in real time (with as much or as little oversight as you want). It's also built to handle upselling available nights to existing guests.

The platform breaks down into five main areas:

• Dashboard: Your bird's-eye view of conversations, bookings, and how everything's performing.

• Properties: Where you manage the nitty-gritty details for each listing — contact info, access instructions, amenities, etc.

• Action Items: A simplified list of any issues guests have mentioned, potentially requiring your attention.

• Messaging: The core of the whole thing — where AI-generated messages live and where you can jump in manually whenever you want.

• Insights: All your conversation analytics, automation rates, guest satisfaction metrics, etc.

Setting Up with OwnerRez (Spoiler: Pretty Smooth)

I use OwnerRez and connecting HostBuddy through their direct integration was quick and easy. They also integrate with a long list of other popular platforms, so this simple process should be available to most users.

Once connected, HostBuddy pulled in all my basic property info — names, locations, guest communication history, the works.

From there, I could dive into each property profile and add the contingency details that don't always live in your PMS — things like backup door codes or physical key locations in case the smart lock malfunctions, emergency contacts, or specific instructions for handling those occasional tech hiccups.

One key feature worth highlighting: the platform scans through your past conversations not just to emulate your communication style, but to learn property details that might not be captured in your listing. Things like quirky check-in procedures, common guest questions, or those little details you've explained a hundred times but never formally documented.

Building Guardrails: You Decide

One of the most important decisions you will make with the software is deciding what sort of guardrails you may want to put in place.

There's an entire section dedicated to "Conversation Settings" that will dictate how the system will react in certain situations.

The most important guardrail is setting how you want HostBuddy to respond if a guest has raised a concern that it can't resolve. These options range from doing nothing and notifying you of the issue to providing the guest with your direct contact information.

There are several other settings available to guide the conversations, as well as an area to give it guidance on general tone. Over time, I've found myself going back to this section to continue molding how I want it to respond.

All of these settings are customizable by property, so you're not tied into one general set of rules across the board.

Reality Check: Garbage In, Garbage Out

Let me tell you about my Wi-Fi disaster, because it perfectly illustrates both the power and the pitfall of this system.

After switching to StayFi at one property, I regretfully failed to update the network name anywhere: my messaging, HostBuddy, etc.

The next guest checks in and you can probably guess what happened next.

An innocent enough message from the guest, "hey, the wifi isn't working" turned into a long back and forth where HostBuddy eventually recommended rebooting the [locked-in-a-cabinet] router.

Reading these messages left me shellshocked. What could have been an easy solution turned into a bad guest experience.

Lesson learned: AI only knows what you tell it, and you've got to keep your data current across all platforms. The good news is HostBuddy has settings to limit what gets auto-answered while you're getting comfortable with the system.

Also, minor gripe: the property selection UI in settings could use some work. I've definitely thought I was updating settings for one property only to realize it applied to the other one. The dropdown doesn't always make it obvious which listing you're editing, especially if your property names are similar. Now I obsessively double-check everything before hitting save.

Smart Templates: My Favorite Feature

Responding to guest messages is a nifty time-saver, but what really caught my eye was the Smart Template functionality.

Scheduled templates from your PMS are stale and can often sound awkward within the context of the existing guest conversation.

HostBuddy solves for this.

You can create templates similar to how you would in many PMS platforms, decide when they go out and under what conditions they get sent. HostBuddy, will tweak the language, however, to fit in the with natural flow of the conversation.

Genius.

If I had one feature request for the HostBuddy team, it would be to develop Smart Templates further. I'd love to be able to create one template for one purpose, but have a repository of information related to timing and conditions for it to reference.

For example, if you want to include messaging for guests with pets, you'd have to create two separate templates. HostBuddy should be able to adjust based on specific criteria, not need a completely separate template for every possibility.

(Hospitable short codes accomplished this in some capacity, but HostBuddy could go way above and beyond those capabilities).

The Money Talk

HostBuddy's pricing is pretty straightforward:

• Pro: $7/mo per property - Essential AI tools for individual hosts and small operators.

• Elite: $10/mo per property - Advanced solution for growing property management businesses.

• Ultimate: $12/mo per property - Enterprise capabilities for large portfolio management companies.

Each plan comes with a free two-week trial (see below on getting an additional month!) and is discounted with an an annual commitment up front.

I opted for the Elite plan initially, and decided I'd re-evaluate if that were necessary moving forward, after I began paying.

There are features in the Elite plan that are not relevant to me, but within each, the number of Smart Templates available is limited.

I do find this pricing structure a bit of an annoyance. I understand some features not being available based on pricing tiers, but to limit the use of this feature seems like an unnecessary restriction.

Here's how to turn your two-week trial into six:

1. Visit HostBuddy.ai to sign up and begin your two-week trial.

2. After completion, proceed to the payment area to activate your account.

3. Use coupon code STRTECHTALK to receive one additional month, and watch your amount due reset to $0.

You can cancel at any time before the month is up and pay nothing, otherwise your account will auto-renew.

Bottom Line: Is It Worth It?

HostBuddy isn't going to revolutionize your entire hosting operation (yet!), but it might just give you back something you didn't realize you'd lost: the ability to actually disconnect without worrying about guests getting radio silence.

If you're only managing one property that you live next to and rarely travel, you can probably skip this.

But if you:

• Travel regularly or manage remotely

• Want consistent guest communication without being chained to your phone

• Like automation but still want to maintain that personal touch

• Have multiple properties with different quirks and requirements

...then HostBuddy might make a lot of sense.

The Smart Templates alone make it worth considering as an alternative to basic PMS automations. Add in the flexibility to customize tone, timing, and automation levels per property, and it starts feeling less like "AI taking over" and more like "finally, technology that actually helps."

Would I recommend it? Yeah, especially for tech-forward hosts who want to stay hands-on without being on call 24/7. Just remember to keep your information updated across all your systems (learn from my StayFi mishap), and don't be afraid to start with more human oversight until you get comfortable.

Your future self — the one actually enjoying dinner without phone anxiety — will thank you.

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@STRTechTalk