1. Good question, but it doesn't appear to have anything to do with the lottery.
2. Are you trying to squeeze him into your visa?
3. What is your question?
You would be wise to talk to an immigration attorney ... these are complex and delicate matter that you are considering.
PROFESSOR OF IMMIGRATION LAW for over 10 years -- This blog posting is offered for informational purposes only. It does not constitute an attorney-client relationship. Also, keep in mind that this is an INTERNET BLOG. You should not rely on anything you read here to make decisions which impact on your life. Meet with an attorney, via Skype, or in person, to obtain competent personal and professional guidance.
Apply through adjustment of status. You can submit form I-485 90 days before your number is reached.
Mr. Shusterman's (former INS Trial Attorney, 1976-82) response to your question is general in nature, as not all the facts are known to him. You should retain an attorney experienced in immigration law to review all the facts in your case in order to receive advice specific to your case. Mr. Shusterman's statement above does not create an attorney/client relationship.
You can include him with your adjustment if status while you both are here legally. Better not risk the consular processing which may interfere with your f1 and his employment as h1.