Admittedly, I've only known two PIs, both who do higher-end corp work, and one insurance investigator...

I know it fiction, but the "scummy, hated by the police PI" seems to be a recurring theme.

Have any LEOs on here actually had negative interactions with PIs? At least, the ones I knew were far to expensive to regularly bump into cops (aside from the insurance investigator, who worked with police quite regularly.)

Might want to clarify the title...

Only one. He had his PI Licence revoked and then became a Scummy Bail Bondsmen. He got that licence revoked too within a few years.

I hired a PI back in 1987 during a divorce and to secure my daughter's future.

The guy was prior military, (OSI) and did a phenomenal job.

I ran into him nearly 30 years later and "brought him up to speed", on what how things turned out, (wanted him to know that it mattered to me, and my daughter) thanked him for his professionalism and his efforts.

There may be some "scummy" PIs out there, but I am ever grateful for the guy I hired.

So, yeah, I am that guy that roots for the home team, the underdog and as cynical as I am, I believe the righteous win in the end.

Maybe not what the OP was looking for, but, I am ever the optimistic pessimist.

During my brief career as a PI, I got along fine with cops.
As Bogey once said:
"There is not a lot of money in it if you are honest".

over the years, I would run into PIs here and there mostly by checking suspicious vehicles or getting called to the same. I'd skeedaddle as soon as I found out they were working to not blow their cover.

I never had a problem with PIs, bail bondsmen/bounty hunters, auto repossessors, etc. They all had their work cutout for them.

A bizarre random thought is something like this...

If an elephant and a ostrich has sex on the moon would the offspring be born or hatched?