Tax Strategist Questions

[James Palassis]

Hello all - I am in the process of building my "team" to hit the ground running in my investing career. Along those lines, I am meeting with a potential tax strategist on Friday. Right now I don't know what I don't know. Any suggestions on what questions I should be asking would be greatly appreciated?

Background: I recently purchased a lot with boatslip in a lakefront community that eventually I would like to build on and AirBNB/VRBO it. Before I proceed with that project, I am wanting to explore student rental investing in a nearby college town. The game plan being to get some cash flow going before tackling a larger expense of the lake house. 

By meeting with a tax planner, I want to explore the following topics. Is this comprehensive enough? Any further suggestions? (These are questions I plan on asking the tax planner, I am not expecting answers to these specific tax questions on this forum):

Can I open an LLC to deduct expenses while searching for the right student rentals? (Wife and I are straight w2 and no mortgage interest, so we are getting crushed).

If I choose not to build on the lake property, can I 1031 it? If I do, do I have to purchase raw land?

Have you ever worked with real estate investors in the past?

Are you or anyone at this practice a real estate investor?

If there are other topics/questions to cover, I am all ears. Thanks everyone!