No one knows for sure even if you talk to a lawyer. There is always risk
evolved. If you have immigration intent, then none of immigration class like
F1/F2/B2 should be granted based on paper. H1/H4 are different since they
allow immigration intent. But in reality, there are cases like those visa
are approved.
It really don't matter what you file, the point is to keep "in status".
Normally you have at least 2 months with pending, plus any appeals. As long
as you don't go over 180 days. But again, it you cannon find a job in 180,
then maybe it's time to find the alternative plan.
There are also cases for H1B transfer with gap and still worked. If the gap
is small, most likely it is OK. But again, if you want 100% sure, it just
doesn't exist.