Best tech stack for managing STR and Mid-Term Portfolio and automating work flows?

Question

Hi everyone — I currently manage a small-to-medium sized rental portfolio that includes both short-term and long-term units, and I’m looking to optimize my tech stack. I am especially interested in any AI backed systems that are working well for you.

Right now I’m using:
• Airbnb (listings & bookings)
• PriceLabs (dynamic pricing)
• Hospitable (automated messaging & calendar management)
• Stessa (bookkeeping & bank account tracking)
• Turno (cleaning coordination)• Innago (mid & long-term rent collection and lease management)
• OneNote (data/records/operations info)

I’d love to hear from other investors/operators about what software/tools you use for:
- Channel management & calendar sync across short & long-term
- Dynamic pricing & revenue management
- Automated messaging and guest/tenant communication
- Bookkeeping / financial tracking / reporting
- Cleaning & maintenance operations
- Documentation / knowledge management

Specifically:

• What tools are working best for you across these functions?
• Are there platforms that combine multiple functions (especially AI-native systems)?
• Have you found ways to reduce the number of separate systems you rely on?
• How are you automating interactions between systems (e.g., integrations, Zapier, APIs)?
• What daily tasks have you fully automated, and how?

What tools are working best for you across these functions?

Are there platforms that combine multiple functions (especially AI-native systems)?

Have you found ways to reduce the number of separate systems you rely on?

How are you automating interactions between systems (e.g., integrations, Zapier, APIs)?

What daily tasks have you fully automated, and how?

Thanks in advance — I’m trying to streamline workflows and reduce manual overhead as much as possible!

Ryan D. · Answer

I run both STRs and LTRs and had a similar stack at one point. What worked for me was slowly consolidating rather than adding more tools. Fewer systems, less syncing, fewer things to break.

I focused on reducing process churn — cleaning schedules, inventory management, tenant communication, contractor coordination, financials all under one roof so there's less hands on deck needed day to day. Every integration point is a potential failure point so the simpler the better.

On the AI side — I'd be cautious. Most "AI-native" tools are just ChatGPT wrappers. Useful for templated stuff but anything that needs context about your specific properties still needs you. I always keep a manual safety net on anything that matters.

Jerry W. · Answer

@Jacob Switzer, nice thread.  I currently have 7 STR and dabble in a few mid term rentals, and have about 60 long term rentals.  We currently just use google sheets for accounting, and Hostfully for managing the STR.  Hostfully does the automatic messaging, but Air BnB has nice messaging as well.  I also use Turno that integrates with Hostfully for assigning cleanings after stays.  I am currently manually setting prices but have used Pricelabs in the past.  It was really nice having reports on other houses, but it took a lot of work to get the prices close to what they should have been.  I am sure it has improved since then.  I am looking into adding automated locks and Remote Lock is being considered, but I think Hostfully has it available through them now.  I am open to suggestions if you have ways to improve.  I need to automate more.  It is just me and one other office person, my accountant, and a couple of handymen for staff.

Araba Ayomide · Answer

The stack question is usually less important than the system built on top of it. Most investors I've worked with have decent tools — the gap is in how the workflow is structured around them. For STR and mid-term you need something that handles the full cycle — inquiry capture, automated response, booking confirmation, and follow-up for unconverted leads — without someone manually managing each step. Happy to share what's worked if you're still figuring out the stack.

Ryan Stomel · Answer

Coming from the commercial side of a mixed portfolio — the STR/MTR automation tools mentioned here work well for residential but the stack gets more complicated once you add commercial leases.

For the commercial piece specifically the gap I kept running into: none of the standard PM tools handle NNN/modified gross lease structures, CAM tracking, or year-end reconciliation cleanly. I ran QuickBooks + Hostaway-equivalent for STR and a separate spreadsheet for commercial CAM for years, which technically works but creates a real mess at year-end.

What finally closed that loop for me on the commercial side was PigJet (pigjet.com) — built specifically for small/mid CRE operators. Handles NNN and modified gross leases natively, tracks CAM estimates vs. actuals per tenant, syncs to QuickBooks, has e-sign built in. For anyone with commercial units mixed into their portfolio, it's worth looking at before you try to force AppFolio or Buildium to handle lease structures they weren't designed for.

Koba Molenaar · Answer

@Jerry W. You've built a very impressive property portfolio. I'm curious to know, you mentioned that you need to automate more — are there any specific tasks (aside from automated locks)?

Jim Johnson · Answer

Great question — you’re already running a pretty solid stack. At that point, optimization is less about adding tools and more about reducing fragmentation and tightening workflows.

A few patterns that tend to work well at your stage:

1. Consolidate where possible (especially STR side).A lot of operators eventually move toward an all-in-one PMS like Guesty, Hostaway, or OwnerRez to replace multiple tools (channel management, messaging, some automation). It reduces handoffs between systems, which is where most friction happens.

2. Separate STR vs mid/long-term systems intentionally.Trying to fully merge them usually creates more complexity. Many keep:

• STR → PMS + pricing + cleaning automation
• Mid/LTR → something like Innago/AppFolio + accountingThe key is syncing reporting, not forcing one system to do everything.

3. Use automation layers sparingly but strategically.Zapier/Make works best for:

• Triggering tasks (booking → cleaning → inspection checklist)
• Syncing key data points (reservations → accounting)
• Alerts (low reviews, maintenance flags, missed messages)Too many automations can actually create blind spots if not monitored.

4. Focus on visibility, not just automation.You mentioned quality control — that’s where most setups fall short. Requiring:

• before/after photos
• standardized checklists
• centralized communication logsoften matters more than adding another AI tool.

5. AI is most useful in communication + ops support right now.Where it’s actually working:

• drafting/responding to guest messages
• summarizing reviews into action items
• organizing SOPs and internal docsLess so in fully replacing core systems.

Most operators at your level don’t win by stacking more tools — they win by simplifying workflows, reducing duplicate inputs, and tightening control points.

If anything, your next step isn’t “what else to add,” but “what can I remove without losing visibility or control.”

Koba Molenaar · Answer

Hey @Jacob Switzer

Thanks for sharing your tech stack. I love seeing what hosts are using and discovering new tools in the process. What immediately caught my attention about your tech stack is that some of the tools you use can be used for multiple functions - which answers you second and third question.

So, yes, there are platforms that offer several key functions. For example, a solid vacation rental software would be able to tackle calendar management, messaging, cleaning co-ordination, some basic bookkeeping/financial reporting, and maybe even dynamic pricing.

While I think having a calendar management tool is essential, I noticed that you're listing only on Airbnb. In which case, a calendar management tool isn't really necessary.

Is there a reason why you're only on Airbnb? Have you considered using other sites for listings and bookings?

Jake Baker · Answer

@Jacob Switzer

The key is to have all your software integrate efficiently with one another and automate as much as possible. For bookkeeping, I recommend QuickBooks Online. Many on the forums will advise against QBO. It can feel like feature overload. The main reason is that it is not initially set up for a Real Estate business like other “real estate-specific” accounting software. It takes a certain level of QB knowledge to set it up correctly. However, QBO has integrations with Hospitable and Airbnb that remove a lot of manual data entry for bookkeeping. Also, most tax preparers are familiar with QBO.

Jonathan Avellaneda · Answer

I have 2 STRs and 1 LTR. I Use Hostaway for everything related to the STRS including messaging, cleaner automation, calendar coordination, guest messaging. Hostaway has AI built into automation for guest messaging. You can choose to autoreply with the AI after training, or just have it draft the message and when you go in to respond send it or edit it before sending. I use pricelabs for pricing , listing optimization, and seasonality. I use quickbooks for the business as it is easy to setup auto-rules for most everything.

For the LTR i use Turbotenant for everything and it has been great.

One thing that i am looking into now, and just starting, is automation of maintenance tasks. Those things that come up when things get broken, but also quartlerly/annual tasks that need to be completed for the home .

David Cherkowsky · Answer

I only have one STR, but I use Hospitable, Pricelabs, and Google Sheets (for bookkeeping) and have most of my operations automated through those systems.

Are there specific things with your current tech stack that are not automated well that you're looking for solutions on?

Best tech stack for managing STR and Mid-Term Portfolio and automating work flows?

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