On student visa working on startup, options for staying in US?

I'm a 25 year old student on F1 Visa (OPTX) that expires in 7 months. I work as a software engineer at a tech company. The company will sponsor me in applying for the H1B visa. I'm also working on a startup with a US citizen. We plan to have the startup sponsor me as well for the H1B visa. Hopefully applying for a concurrent H1B visa (source: https://www.am22tech.com/concurrent-h1b-multiple-jobs/) will help improve my chances of getting picked during the lottery. I'm also considering a US O-1 visa and EB-1 visa, but might not have the right credentials. I have a Master of Sciences in Computer Engineering with Master Thesis in Machine Learning. I've built sophisticated logistics tools that generated $500k+ of annual recurring revenue in my role as a software engineer. The startup I'm working is launching soon and will be a B2B SaaS that should generate good cash flow. For who have been through similar situations or with immigration knowledge, your feedback and advice would be greatly appreciated:

1. What are my best options for staying in the US?

2. What other options do I have for staying in the US?

3. For an H1B visa, is there any downside to applying through multiple employers for different positions at different companies?

4. Do I have a shot for the O-1 or EB-1 visa?

5. Is it worth exploring options in Canada? If so, what is recommended for my situation?