Then refis, sales, or tax time turn into cleanup projects.A few common patterns I see:• Waiting until year-end to update books• Property manager statements not tying to bank activity• No clear property-level view of cash flowNot here to pitch, just sharing observations and curious if this lines up with others’ experience or if you’ve found systems that work better.

I patterned this structure after some other larger operators I've worked with. 

What really stands out to me is your point that the money is made before the purchase, underwriting operations, turnover costs, systems, and guest experience, not just the acquisition price.I’ve been noticing the same pattern in outdoor hospitality as well: the operators who win are the ones who design systems around experience delivery and repeat guests, not the ones hoping platforms do the heavy lifting.

.)- Review previous rent ledger for patterns to be aware of, note their lease in PMC software- Try to convert to our Lease, to make it easier on our staff (we don't tell tenants they don't have to do this)- Opportunity to renew/extend lease with increase?

Quote from @Julien Hill: Over the last 18 months working with mortgage brokers on DSCR deals, I've noticed a pattern with the partnerships that actually work long-term.It comes down to execution fundamentals that protect everyone involved, including the broker's reputation, the investor's timeline, and the deal itself.Consistent execution looks like the below:Response time matters - Initial response within hours, not days.

This will allow you to compare line items and over time, patterns will emerge, helping your confidence with estimating.Good luck!

Doesn't appear either would be the case given your fact pattern.

That said, based on my experience working with real estate bookkeeping clients and using AI tools internally, AI still has meaningful limitations.AI is good at recognizing patterns, but bookkeeping—especially for real estate—is full of nuance: distinguishing repairs vs. improvements, properly handling owner contributions and distributions, allocating expenses across properties, class tracking, loan activity, depreciation-related items, and state-specific considerations.

A pattern has started, and now he' testing the waters to see what he can get away with in the long run, which means you no longer have authority in the relationship.

I think we see a pattern here.