need to go for stamping- advice needed

[odlh92]

here is the sequence- do I need to be aware of something or worry about something? its been 5 years and I really want to go back home for a trip.

came to US on F1 to do MS

Converted to H1

went to India and got visa stamped in 2005

came back, switched jobs h1 transfer 2006 (top firm consulting for Morgan Stanley)

switched jobs again in 2007 for a hedge fund (full time no consulting )

2009 went back to school NYU for second Masters- COS approved from h1-f1

on OPT right now working for a hedge fund (full time no consulting bs) (ead card for 1 year)

h1b already approved (would be sixth year) starting feb when OPT ends

all GC work in order ready to be filed the day I switch to h1

All paperwork - COS, previous i797, employment verification (current and past), degrees.. in order.

so all in all I have 2 Masters from the US, work as a direct employee at a prominent family investment office hedge fund in NYC (no consulting).

clean record- dont even have a parking ticket violation.

its unfortunate we have to be so paranoid about going home.