If Trump offers Putin enough of the good stuff like unfreezing the Kremlins funds all over the world, allows Putin to seize the assets of countries that 'stole' from it, like luxury yachts etc., I would be nervous right now if I was Iran.
As you mentioned, Russia has done this to Iran three times already, with a 4th time likely on its doorstep.
The only possible exception that I see is if these two leaders agree that Russia supply, and continue to supply, 'vanilla' versions of arms to Iran.
This would enable Russia to save face viz-a-viz its current and future arms customers.
BUT, by doing this, the supply of 'vanilla' arms to Iran would likely ignite a rush for modern US arms to be sold all over the region up there. Thus, increased US exports, increased employment, increased funds flowing in, content voters and general populace, and last but not least, increased US control of what purchasers of its arms may or may not do with these.
Yup - you snooze you lose.
Piet.
Iran arms itself or not, regional countries will continue arming themselves because for one simple reason .... They can! Not the thread for it, but Iranian strategic-level military doctrine is obsolete as Iranian leadership is still stuck in merging national security with diplomacy while everyone else moved to more modern peace through power doctrine. Countries are arming themselves like crazy with more and more lethal tech, all the while they are still part of the global community. Iran checked itself out from all of this long ago. Israel won't stop filling their bases with more and more F-15, F-35s armed with newer and newer ALBMs. PGCC won't stop, Turkey won't stop importing western tech even with its massive debts. Iranian leadership failed to modernise their thinking.
- They decided to use the nuclear program as a bargaining chip in "talks" instead of weaponizing it and moving on decades ago. You do not put your own security or lifeline on the table as a bargaining chip when talking to a much superior enemy. They learnt nothing from Iraq, Syria, Libya.
- They refused to understand that Russia and China wont support them so they have to find alternatives for tech. I wrote above about Russian betrayals towards Iran for 35 years now. Russia looked for its own, Iran did not.
- They killed IRIAF to the point that we are now cheering an AT firing an export version sidewinder in "Air-Drills" featuring 50 years old airframes. In a real war these AT's wont even survive two mins against the actual enemy in air. Another PR stunt.
- They refused to import key TOT/LP which other countries chased like fighter and supersonic CM engines, airborne radars, armament combat suites etc. Instead, corruption ran rampant, Supreme leader+Majles were fooled into funding cash pit meaningless or dare I say fake projects in combat aviation.
Tazarve Trainer - Crash+abandoned.
Yasin AT - Crash, not a single flyable airframe exists in 7 years.
Shafagh AT - never left mockup stage.
Azaraksh - 3 airframes, program abandoned.
Saeghe-I/II - 6 airframes, program abandoned.
Kowsar - 5 Airframes in 8 years, dozens of airframes rusting on Assembly lines.
Qaher - not a single flyable airframe (Fake project) in 13 years.
IrAn-140/Simorgh - Crashes, 2 airframes exist in 20 years.
F-14AM program - 2 exists.
F-4E/D Dowran Program - handful of upgrades.
Fakour-90 BVR - Limited to 2 x F-14AM airframes, will retire with it.
Azaraksh HOBS WVR - never seen with IRIAF, still using obsolete AIM-9J.
OWJ Turbojet - 10 exists on 5 kowsars.
Jashesh Turbofan - Never left the prototype stage.
Stealth ALCM - never left the mockup stage.
List goes on and on.