The lawyer's opinion should be heeded. For second opinion, consult with another lawyer. We do not know all the facts to address your very fact specific situation.
The information contained in this answer is provided for informational purposes only, and should not be construed as legal advice on any subject matter,not should it be viewed as establishing an attorney client relationship of any kind.
You need to pose all of these fact specific questions to your employer's immigration lawyer or lawyer of your choice during a paid consultation.
Kindly be advised that the answer above is only general in nature cannot be construed as legal advice, given that not enough facts are known. It is your responsibility to retain a lawyer to analyze the facts specific to your particular situation in order to give you specific advice. Specific answers will require cognizance of all pertinent facts about your case. Any answers offered on Avvo are of a general nature only, and are not meant to create an attorney-client relationship.
Since H-1 petitions are granted through a lottery you should apply every time you can. And since you will need an attorney for the H-1 you need ask these questions of him/her rather than a blog.