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Results (10,000+)
Bruce Tieu What’s Been the Hardest Part of Managing Your Airbnb or STR?
10 November 2025 | 8 replies
But I’m curious what it looks like for others.What’s been your biggest pain point — guest messages, cleanings, maintenance, or something else entirely?
James Jackson Seeking Local Builder Mentorship — Foundation Process (Alabama)
6 November 2025 | 5 replies
One of my biggest pain-points starting out in New Construction that I sought up people to teach me the process... and like you, I was willing to volunteer my time.
Bobby Andrews Need an appraisers eye on a cash out refi
6 November 2025 | 14 replies
Quote from @Bobby Andrews: @Erik Estrada Still working on it - it's been painfully slow.
Bailey Rankin Furniture frustration, deep pockets, & budget strategy. Is contract grade worth it?
2 December 2025 | 25 replies
For those of you with a large STR portfolio, I'd love to hear your biggest pain points when in comes to furniture.
Lolo Druff First time landlord Renting to Section 8
17 November 2025 | 11 replies
, case manager responsiveness (A good one makes your life easy, a bad one is pain).Make sure your PM knows how to pre-inspect and submit paperwork fast. 
Stuart Udis Tight Hospitality Lending & Landlord Negotiation Leverage
22 November 2025 | 5 replies
Appreciate you sharing the playbook, lots of landlords could avoid painful lessons by understanding this shift.
Satya Surendra Property Management - what value are they adding
24 November 2025 | 13 replies
Hey there @Satya Surendra - I recently switched to a property management company for two of my South Side Chicago properties and I honestly feel your pain......but I believe the right property manager can save you money in the long run with the right preventive maintenance and tenant screening.I had to go through a cash for key situation and it took 6 months of to finally get a new tenant....I think that would have been avoided had I had the property manager at the time because I wasn't giving the property the attention it needed.If you have the time and bandwidth I suggest self managing
Jeremiah Dunakin Showing process, do you show property first or have credit/employment ran
25 November 2025 | 25 replies
That said screening tenants has been a pain in the butt kinda.
James Jones How We Manage 20+ Rentals Across Multiple LLCs Without Chaos
9 December 2025 | 32 replies
That’s the invisible clutter that makes tax season painful and scaling nearly impossible.
Jacob Hoying Validating an idea: Pre-built, updated financial models for investors?
3 November 2025 | 0 replies
The key differentiator is that these models would be constantly updated for things like:Changing mortgage rate formulas and lending rules.New tax laws and depreciation rules.Integration with current data sources for things like rental comps or maintenance costs (where possible).New model types based on emerging strategies.The goal is to save you the hours of building and, more importantly, maintaining your own spreadsheets.I'd be incredibly grateful if you could help me with any of these questions:The Pain Point: Does manually updating your analysis spreadsheets for rule changes feel like a chore?