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Lastly, I'm also contemplating expanding it with a Tempi module later for enhanced clocking and modulation options.

I think it's a toss up between Tempi and Pams - the interfaces are quite different etc... try to work out which one you'd rather work with through watching videos and reading the manuals - Tempi is more button combination presses and Pams is more menu divey (although quite shallow and easy to learn - all channels have the same menu - but the 'programming' interface is relatively basic - the new screen - on the Pro - is apparantly much better and more informative than just some LEDs)

Now, I have a few questions:

1. Despite having been in audio production and synths for 20+ years, how hard is this system and modules to learn?

there'll definitely be a learning curve - take it slowly etc... you'll get there - it's not much different than vcv rack - except you'll have a limited number of module and a limited number of patch cables... and be able to physically control 2 differnt knobs at once...

2. Is this system a good starting point for a modular noob and my objectives?

the tape and sound machine - don't know - maybe - the rack above - imo too much to start with and very heavily leaning towards too many voices and effects and not enough moudlation and utiliites - see my signature for some hints!

3. Can I easily sync Tempi with my DAW (Cubase) to start/stop my modular rig with my arrangement?

probably - I use a kick sample in Logic for sync - played from my audio interface (es8) into PNW - works perfectly... I've set up Pams to start/stop/reset based on this clock... I've also heard of people using the run input similarly... I'd suspect that tempi can work the same - you may need some amplification for the clock etc...

4. Is it possible to reset the units clock when starting, stopping and resetting the playhead position?

see above answer to 3

5. Can this rig somehow accept other types of MIDI, like notes from my NI S88 keyboard? What options are available or what additional equipment is needed to do this?

depends on the midi->cv interface - I'd do some more research before committing to one - the mutant brain - now made by Erica Synths is reputedly a very good and versatile example - also available as a stand alone unit the cv.ocd - if rack space is an issue

6. Are there real risks of damaging any unit/s through improper patching (e.g., outputs into outputs)?

not really with most modern modules - this may have been an issue in the past - although it may also be an old wives tale to some extent - I've accidentally patched outputs to outputs many times and had a problem... (I have a reasonable number of the modules that you have in this rack - especially the mutable ones)

hope all this helps!