I started looking into more things a LLM (large language model) would be capable of doing and started working on a couple features to help with some of the repetitive data entry I was doing every month.I'm curious about learning how people do bookkeeping and some of the things they dread doing?

We have our go-to lenders, bridge lenders for complex deals, and brokers who understand our needs and fight for us.

I’d focus on simple buy-and-hold in landlord-friendly Midwest markets, build a tight boots-on-the-ground team, and let consistency beat complexity.

I had one for years that I liked, but as he grew and purchased a couple of other practices, he pawned me off on a couple of low-level underlings because we weren't big enough or complex enough to warrant big bills.

Successful operators maximize offseason programming (events, summer activities) to stabilize cash flow.Waterpark ResortsWhat defines them:Waterpark resorts include indoor or outdoor aquatic facilities of at least 10,000 square feet, featuring slides, pools, and interactive attractions designed to drive demand.Investor considerations:• Family-oriented demand with strong repeat visitation• Indoor parks can reduce seasonality• Water attractions significantly boost length of stay and ancillary spendKey risks:• Substantial upfront construction and mechanical costs• Ongoing safety, staffing, and maintenance requirements• Higher insurance and operational oversightInvestor takeaway:Waterpark resorts function as entertainment-anchored hospitality assets.

Finally, take copious photos of every room, every fixture, every appliance that you are providing, every door/door jamb and any special or unusual features to document the move in condition.

I suggest joining Philly centric groups and meetups to learn the many nuances of our complex market and how to manage things like tenant relations and repairs.

I recently reviewed a panel discussion from Phocuswright featuring senior leaders from Airbnb, Marriott, and Casago, and it offered a clear look into where short-term rentals are heading.A few themes stood out:• Airbnb is building a broader hospitality ecosystem through services, experiences, and hotels• Marriott is expanding deeper into professionally managed homes with strict operating and brand standards• Arbitrage-heavy models like Sonder were called out as fragile in changing market conditions• The industry is moving away from “any door will rent” toward fewer, higher-quality, better-operated propertiesMy takeaway from this conversation:Short-term rentals are moving away from being just alternative lodging and toward full-scale hospitality.Operators who focus on quality, systems, local expertise, and guest experience will win.Those relying on thin margins, arbitrage, or volume without standards will struggle.How we’re implementing this in our property management businessInstead of chasing door count or volume, we’re doubling down on:• Property selection over scale, only onboarding homes that can meet hospitality-level standards• Operational systems, including standardized inspections, preventive maintenance, and guest communication workflows• Local expertise, with boots-on-the-ground teams who can make real-time decisions and recommendations• Experience-driven stays, layering in services, amenities, and curated local recommendations beyond just the stay• Owner alignment, working only with owners who understand that quality and consistency drive long-term performanceThe goal isn’t to manage more properties.It’s to operate better properties.Curious how others here are approaching this shift:• Are you adjusting your model in response to where the industry is heading?

Having said that, I will offer that there are a lot of sellers who want to sell without drama and complexity - and buyers who are ready to buy quickly as long as it can be done without drama and complexity. 

Just enter fence in “keyword” search if it’s not listed under “features”.