strategy vs chop block

Yeah, tough question and a tough nut to crack.  If it was easy to return those balls, people wouldn't play that way.  My worst losses are against pips blockers...I'm capable of losing to someone under 1500 if they patiently play that style.  Here are some things to try:

1. Serve long and flat to the backhand (assuming that's the pips side).  See if the pipper can take a long no spin ball and put it back well enough to keep you from attacking.  The counter to that serve (if your opponent backs up) is to serve short no spin to the middle forehand or even wide short forehand if your opponent insists on chicken winging everything.

2.  Take the spin out of everything.  Don't put on any spin that will be used against you.  Tap the ball back and test their patience.  I could do this but choose not to.

3.  This one is called up/down.  Serve a moderate, long backspin.  Force your opponent to play it aggressively.  If they block it back, you should be getting back a light topspin to attack.  Continue to alternate top and backspin so you're always working against the spin.

4.  Get good enough to rip everything and simply overpower your opponent.  This is the right way, but a difficult way.

The key is to note how your opponent primarily wins points and whether he takes advantage of things other than your point ending mistakes.  For example, if you pop the ball up high to his forehand or backhand, what happens?  If he doesn't attack attackable balls, then you are under no pressure to attack - your job is then to make him give you opportunities or goad him into errors.

If he attacks and does so consistently in a way you can't consistently defend, then you have a bigger but still controllable problem as he clearly doesn't want to attack but will do so if necessary or easy.

The basic idea is to note the spin inversion of the rally - when you topspin to the pips, the next ball will have light to heavy backspin, depending on how powerful your spin was and how skillful the pips player is.  Then you push that one or loop that one again.  If you push it, then the return will have light to heavy topspin, depending on the skill of the pips player but more importantly the quality of your push   So you can topspin that ball with your light or heavy topspin stroke, including a smash.  And so on. Note your influence on the spin that comes back

You haven't played a good pips blocker then.  They can block heavy topspin pretty short.  And you have to know when to push.

I doubt they can block heavy deep topspin short though (short meaning double bounce!). If it goes out of the table you can always reloop it. Any backspin can always be overcome by sufficient pushing of the legs.

For me if I generate a lot of topspin I can be guaranteed to get good backspin back, so I know at least that I'm playing against backspin. After that it is a battle of consistency.

Pushing could be a good strategy, but to me it complicates the spin which I don't like. It also opens up angles for the pips blocker to use against you. 

A consistent control looping strategy could reap a lot of dividends. I don't think someone like Pushblocker likes to play against control loopers too. 

Okay.  Hopefully, you will play against these guys and post a video.  A lot of strategies work, but in my experience, repeated looping with heavy topspin when you and the blocker are at the same level is one of the less smart ones to put it mildly.  They are trying to block off the bounce so yes, they can often block deep topspin short, not because it is easy, but because their style accidentally does it.

One of the strengths of this style is that their spin shots don't have the same trajectories as inverted spin shots.  Balls will be low without arc.

true, but most of the very backhand  orientated pushblock players don't really have a good forehand loop. The ones that do can beat you.

Eventually I have to try to punish him for that by twiddling back and attacking that high ball. But you have to be quick in noticing that.

Any time I see the tips visibly shinier than the sides of the pips, I know I'm not going to get a consistent output based on my input.  That's where my strategies seem to break down.

I like your strategy. Not sure if I am skilled enough to implement it - probably not. I noticed when he plays high level players that is what they do (we are talking International/National level players) - they loop to his backhand with power and force him off the table or cause his chop block to go long. But he told me I don't have the power to drive him off the table.