Thanks all, I also reached out to the Ultimate assistant and they contacted the station manager for me. I learned quite a bit so I'll share it here in case others have the same (or similar) question. There is a transit option but:
Arriving from international flight and have onward connecting on the same day to a 3rd country (international flight) with both full service airlines = Transit (even if pax holds separate tickets)
Arriving from International flight and have onward connection on same day to domestic destination = Not applicable for transit
Arriving from international flight and have return flight on the same day = not applicable for transit
Arriving from international full service flight and have onward connection on the same day to 3rd country (international ) with Low cost carrier VV = not applicable for transitTherefore if Pax :
arriving by KL835 SIN DPS and on the same day have KL836 DPS SIN on separate tickets = is not eligible for transit, pax need to CIQ in DPS
Arriving by KL835 SIN DPS and on the same day have connection with QF DPSSYD (for example on full service carrier) = eligible for transit even if on separate ticket.
Arriving by KL835 SIN DPS And on the same day have connection with LION Air DPSMEL (for example on low cost carrier) = not eligible for transit, pax need CIQ in DPS
Arriving by KL835 SIN DPS and on the same day have domestic connection = not eligible for transit.
However, they did inform me that with the new eGates if I got a multi entry D type visa or E-VOA, I wouldnt have to queue for immigration. I believe that is the solution and at around $90, far more cost effective than the VOA 15 times
Since I will be doing this back to back, I should also know the day before if there are any issues with my next day's boarding pass thanks to the 30 hour checkin window. Is it ridiculous, obviously... but is it doable, I think it just might be
