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

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

Jacob Switzer
New to Real Estate · St. Louis · Member since 2020 · 5 posts · 11 votes

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:

  1. What tools are working best for you across these functions?

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

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

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

  5. 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!

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Ryan D.
Investor · Portland, OR · Member since 2026 · 67 posts · 35 votes
5mo

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.

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  • David Cherkowsky
    Investor · Alexandria, VA · Member since 2023 · 92 posts · 52 votes
    7mo

    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?

    2Reply
  • Jonathan Avellaneda
    Investor · Puyallup, WA · Member since 2021 · 73 posts · 53 votes
    6mo

    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 .

    1Reply
  • Jake BakerBusiness Member
    Flipper/Rehabber · San Diego, CA · Member since 2020 · 1k+ posts · 695 votes
    6mo

    @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. 

    [email protected]
    BookkeepingRE - Bookkeeping for Real Estate & Service-Based Businesses58 Reviews
    WebsiteView Page
    1Reply
  • Koba Molenaar
    Cape Town, South Africa · Member since 2026 · 23 posts · 13 votes
    6mo

    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? 

    0Reply
  • Jim Johnson
    Real Estate Agent · Memphis · Member since 2026 · 552 posts · 318 votes
    6mo

    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 + accounting
      The 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 logs
      often 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 docs
      Less 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.”

    0Reply
  • Jerry W.Pro Member
    Moderator
    Investor · Thermopolis, WY · Member since 2012 · 4k+ posts · 4k+ votes
    6mo

    @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.

    1Reply
  • Koba Molenaar
    Cape Town, South Africa · Member since 2026 · 23 posts · 13 votes
    6mo

    @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)?

    0Reply
  • Ryan Stomel
    Property Manager · Calabasas, CA · Member since 2026 · 141 posts · 67 votes
    5mo

    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.

    0Reply
  • Ryan D.
    Investor · Portland, OR · Member since 2026 · 67 posts · 35 votes
    5mo

    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.

    3Reply
  • Araba Ayomide
    Member since 2026 · 52 posts · 16 votes
    5mo

    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.

    0Reply
  • Jerry W.Pro Member
    Moderator
    Investor · Thermopolis, WY · Member since 2012 · 4k+ posts · 4k+ votes
    3mo

    @Koba Molenaar, sorry for the delay, I think I need to set up a website that lists properties available for rent now or coming soon, gives the application for folks to fill out, and allows current tenants post repairs needed or suggestions to improve properties.  Probably some type of inventory management that shows how fast I am using cleaning supplies and paper products and automatically orders large batches of it.  Maybe something that sends a message to he cleaner like, please check to see if the barbque grill needs cleaned, or check to see how many dishwasher pods are left and message us about it.  Do you need more pepper or salt for filling the shakers?  Etc.

    1Reply
  • Kehinde Filani
    Developer · Houston · Member since 2026 · 9 posts · 1 vote
    3mo

    Thanks for sharing such a detailed breakdown of your tech stack! It sounds like you’ve already got a strong system in place. A few things I’ve seen work well for rental operators trying to streamline:

    • Automating lead and guest follow-ups through a single CRM or automation platform can save a lot of time and reduce missed communications.
    • Using integrations (Zapier, Integromat/Make) to connect your booking platforms, cleaning/maintenance schedules, and financial tools can cut down on repetitive manual updates.
    • Some operators are consolidating messaging, task management, and pipeline tracking in one place to reduce tool fatigue—especially with AI-driven workflows that handle reminders, tenant messaging, and recurring tasks.
    0Reply
  • Kehinde Filani
    Developer · Houston · Member since 2026 · 9 posts · 1 vote
    3mo

    Thanks for sharing,  That sounds like a game-changer—especially centralizing cleaning, scheduling, and bookkeeping. I totally get the app fatigue; even a few tools can feel like herding cats. Curious—have you found ways to automate lead follow-ups or tenant communications on top of TurnFlow?

    0Reply
  • Andrea Fernandes
    Specialist · Goa, India · Member since 2026 · 175 posts · 36 votes
    3mo

    Hey @jacob great thread — your stack is already pretty solid honestly.

    One thing worth looking at is the gap between your tools. You've got Hospitable handling STR messaging and Innago handling MTR rent collection, but nothing connecting them to a central operations layer. That's usually where things fall through — a cleaning job not triggered after a booking, or a maintenance request sitting unnoticed because it came in through the wrong channel.

    n8n is worth exploring for question 4 specifically. It's open-source, sits between your existing tools, and can automate the handoffs that Zapier charges a premium for at volume. I've used it to wire together booking confirmations, cleaning triggers, tenant notifications, and Google Sheets logging without replacing any of the core tools.

    For consolidation — Notion or a custom Airtable base can replace OneNote and give you a proper ops dashboard with automations built in.

    Happy to go deeper on any of this if useful.

    — Andrea

    0Reply
    • Rauph Souleimanov
      Investor · FL · Member since 2023 · 36 posts · 11 votes
      3mo
      Quote from @Andrea Fernandes:

      Hey @jacob great thread — your stack is already pretty solid honestly.

      One thing worth looking at is the gap between your tools. You've got Hospitable handling STR messaging and Innago handling MTR rent collection, but nothing connecting them to a central operations layer. That's usually where things fall through — a cleaning job not triggered after a booking, or a maintenance request sitting unnoticed because it came in through the wrong channel.

      n8n is worth exploring for question 4 specifically. It's open-source, sits between your existing tools, and can automate the handoffs that Zapier charges a premium for at volume. I've used it to wire together booking confirmations, cleaning triggers, tenant notifications, and Google Sheets logging without replacing any of the core tools.

      For consolidation — Notion or a custom Airtable base can replace OneNote and give you a proper ops dashboard with automations built in.

      Happy to go deeper on any of this if useful.

      — Andrea


      n8n is underrated for this, been using it to connect tools that don't talk to each other natively. way cheaper than zapier at volume and way more flexible
      0Reply
  • Andrea Fernandes
    Specialist · Goa, India · Member since 2026 · 175 posts · 36 votes
    3mo

    @Jerry W. 

    - the cleaner checklist and inventory automation you described is actually straightforward to set up on top of Hostfully — a workflow that fires automatically after each checkout, sends your cleaner a checklist with specific questions (BBQ clean? Dishwasher pods? Salt/pepper?), collects their responses, and flags anything that needs restocking before the next guest. No new tools needed, just connecting what you already have.

    The automated lock piece Hostfully offers through RemoteLock is solid too — guest gets a unique code at booking confirmation, code expires at checkout automatically.

    With just you and one other office person across 67 doors, where does most of the manual time go right now — is it the cleaner coordination, the LTR side, or something else entirely?

    — Andrea

    1Reply
  • Jillyan MacMorris
    Rental Property Investor · Chicago Suburbs, IL · Member since 2021 · 72 posts · 54 votes
    2mo

    I love this question and these answers! I am a midterm rental investor and I use a lot of similar tech to you. I did recently downsize Turno into Hospitable’s newly upgraded marketplace since I can now invite my existing cleaners. It covers a lot of the same functionality with a lower fee. You have to upgrade to mogul, but that also helped me to streamline my cohosting services with owner portals included.

    And then I use Baselane instead of Stessa. There are arguments both ways and I’ve only ever used QBO before Baselane. I have loved combining the banking and accounting together and how well the AI speeds things up even faster. It’s been such a clean pairing for my investing.

    Thanks for posing this question! Some of these answers are giving me ideas!


    0Reply
  • Jeffrey Abraham
    Lender · United States · Member since 2020 · 177 posts · 26 votes
    2mo

    Your stack is already solid. I'd look at adding automation with Zapier or Make to connect everything, and consider an all-in-one PMS like Hostaway or Guesty if you want to reduce the number of apps. Automating guest messaging, cleaning schedules, accounting, and maintenance tickets can save a lot of time as your portfolio grows.

    0Reply
  • Jerry W.Pro Member
    Moderator
    Investor · Thermopolis, WY · Member since 2012 · 4k+ posts · 4k+ votes
    2mo

    @Andrea Fernandes, there is so much hehe.  Keeping cleaners on track.  Organizing deep cleans between guests, picking up a few cleans when cannot get enough cleaners for 6 or 7 turnovers.  We get maintenance calls we forward to handymen or plumbers, guests requesting early checkin or checkout , or both hehe.  Doing lease renewals, doing scope of work projects on newly acquired houses,  Planning the new interior on our next vacation rental.  Checking up on contractors, Taking rent and making deposits, paying bills, advertising empty house, doing backgrounds on potential tenants.  Getting workers to do mowing, weed spraying, staining fences and decks.  Ordering in supplies for STRs, restocking houses.  Taking calls for private bookings from old guests who have no internet skills. hehe lots

    0Reply
  • Jeffrey Abraham
    Lender · United States · Member since 2020 · 177 posts · 26 votes
    2mo

    Sounds about right! 😂 The biggest thing is having good systems and reliable people. Automating what you can and building a dependable team of cleaners, contractors, and vendors makes a huge difference. Property management is definitely more than just collecting rent!

    0Reply
  • Eduardo Cavasotti
    Investor · Charleston, SC · Member since 2018 · 196 posts · 84 votes
    2mo

    The trap is automating around 8 systems instead of deciding which record owns each fact.

    For a mixed STR and mid term stack, I would define the source of truth for 5 things: booking, deposit, cleaning, maintenance invoice, and owner financials.

    If those 5 do not reconcile without a weekly copy and paste session, the stack is not automated. It is prettier manual work.

    0Reply
  • Mike Shemp
    Rental Property Investor · Stewartsville, NJ · Member since 2016 · 418 posts · 280 votes
    2mo

    We use Hospitable with their dynamic pricing to simplify things.  We don't use any third party cleaner software and instead just add cleaners as a TeamMate in Hospitable and they get notified for every new, update, cancellation.

    For gaps in functionality at Hospitable we use Zapier and Claude Cowork.  Claude Cowork can connect to the Hospitable MCP server, so Claude can get access to all your data.  As a simple example I made a skill called "PaymentReminders" for our direct booking guests that book through me.  It runs each week and if reservation is 40-35 days out, emails them a payment reminder.  31-34 days out emails another payment reminder, but removes the paper check as an option in the email.  At 30 days out it lets them know their reservation will be cancelled the next day.  At 29 days out, it cancels their reservation and sends an email to encourage them to make payment asap before another guests books their week.  It also talks to them as my AI assistant so they don't get mad at me when their reservation is cancelled....I didn't cancel it, my AI Assistant did.  ;-)

    Hope that helps.

    Mike

    0Reply
  • Andrea Fernandes
    Specialist · Goa, India · Member since 2026 · 175 posts · 36 votes
    2mo



    @Jerry W. Haha, that's a lot — but it's also really useful because most of what you listed actually clusters into a few systems, not 20 separate problems.

    The biggest wins for someone running lean (just you + one office person) are usually the ones that eat time daily rather than the one-off stuff. From your list, three jump out:

    1. Cleaner coordination + restocking — this is the checklist/inventory flow we talked about, fires automatically after each checkout
    2. Maintenance call routing — instead of you manually forwarding calls to handymen/plumbers, requests get logged, categorized, and auto-routed to the right vendor with the details already attached
    3. Early check-in/checkout requests — these can be auto-approved or auto-declined based on rules you set (e.g. auto-approve if no same-day turnover), so it's not hitting your phone every time

    Lease renewals, tenant background checks, and the one-off stuff (interior planning, contractor check-ins) are probably fine to keep manual — not every part of the business needs automating, just the repetitive daily noise.

    — Andrea

    @Jerry W.

    0Reply
  • Obinna Ezeilo
    Frisco, TX · Member since 2019 · 17 posts · 2 votes
    2mo

    Solid stack already — Hospitable + Turno + PriceLabs covers a lot of the operational load.

    One gap I see a lot with setups like this: none of these tools talk to each other natively, so you end up doing manual cross-checks (e.g., confirming a cleaning got scheduled after a booking, or catching a pricing mismatch before it syncs wrong). That's usually where n8n or Zapier-style automation earns its keep - not replacing any of your current tools, just wiring them together so a booking event in Airbnb can auto-trigger a Turno cleaning task and a Stessa expense log without you touching anything.

    If you're managing this solo or with a small team, I'd prioritize automating the handoffs between tools before adding anything new - that's usually where the actual time leak is, not in any single tool being weak.

    0Reply
  • Giuseppe Cavucci
    online · Member since 2026 · 99 posts · 44 votes
    2mo

    Solid stack already, curious what others say on the AI-native consolidation side too. One gap I don't see covered in your list though: capital reserve planning, tracking when the roof, HVAC, water heater etc will need replacing and what to actually set aside monthly for it. Stessa handles the bookkeeping and bank tracking side well, but that's backward looking, income and expenses that already happened. None of the tools you listed seem to touch forward planning for major system replacements specifically.

    Might not be a priority depending on portfolio age and size, but with a mixed STR/mid-term portfolio, worth having somewhere separate from day to day cleaning/maintenance ops, since capital planning is a different time horizon than turnover coordination.

    I built a small tool called ReserveTrack for that specific piece, since I kept hitting the same gap. Might be worth a look if it's something you're not already tracking somewhere.

    1Reply
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