I've got the opportunity to log some hours on the cheep flying a tail dragger. It'd get me the endorsement in my logbook and some old timers swear by the improved capacity of pilots who have spent time in these. Mostly the rudder control.

I'll pitch the question to the experience of this forum... taildraggers... worth it or pass?

Worth it... it makes you a real pilot... it's get old watching social media videos of x-w landings and everyone praising the crappy landing...

Conventional gear will or will not make you a good pilot: that is, it will, and it will not.

What it won't do is instill judgement or common sense, both of which are necessary regardless of what undercarriage rests beneath. A conventional gear airplane matters during taxi and briefly during a transition on landing...otherwise it really makes no difference.

You used the word "cheap," which is the rating of quality. Avoid cheap airplanes. Fly inexpensive ones all you can. There's a big difference.

Flying conventional gear isn't a superhuman feat. It can prove a bit less forgiving of poor technique or error, but there's far too much legend and lore flying about and too little truth. Tricycle gear tends to permit laziness, whereas conventional gear requires you to stay with the airplane throughout the landing and ground operation, instead of leaving the cockpit for a sailboat in the Bahamas, the moment the mains touch down.

A taildragger has no tailwheel; it has a skid. Conventional gear uses a tailwheel.

Why slipstream effects to tail wheel plane?

Any thoughts as to if you think the tailwheel endorsement will be a plus on the resume/interview process?

None, whatsoever. Nobody will ever ask, unless you're applying for a job that flies conventional gear.

It can prove to be an ice breaker when your interview begins with a logbook review, and your logbook has a picture of a unique airplane that you've flown.

A conventional gear endorsement really has no place on your resume, unless you're applying for a conventional gear job, in which case you're expected to know what you're doing, and the endorsement is a formality that you should already have.

I don't have a conventional gear endorsement. Nobody has ever asked if I have one. Or cared.

An endorsement is not a rating.

Also looking at getting some time in a pontoon seaplane. I'm hoping a diversity of experience in aircraft will be of some help in my skill development as well as in the interview/hiring process. Are these just icebreakers at best? Does a pattern of variety of aircraft help at all?

Help with what?

No, they're not icebreakers. They're aircraft. They're experience.

What you do with that experience is up to you.

If you're talking about airline applications, there's really no place to list float or conventional gear experience, nor will anyone care. Single engine or multi engine, turbine or not. That's about it.

I learned to fly in a J-3 cub. I took my commercial checkride in a seaplane. Flying floats is about as much fun and enjoyment as one can have in a light airplane, with clothes on.

Again, it's experience. What you do with it is up to you.

While an endorsement won't show up on your applications or most of the time on a resume, a seaplane rating will. Few will care, though.

Absolutely.

IF it is multi engine, turbine, or requires a type-rating. Otherwise it's just hours.

Varying your experience is always a good thing.
Anything that enhances your skill is also a good thing.

Yes, if you have nothing else to do this weekend go for it.

But as others have said, if time and money is limited, might be better spent on more career-specific training.

Also careful taking GA checkrides which you don't have to take... a random GA bust will follow you forever, and impact your career progression.