Since you're looking to expand into Florida and other states, I'd recommend starting by narrowing down your focus:Market Research – Florida has great opportunities, but each state and city has different laws, taxes, and demand drivers.

If you need an LLC for tax reasons later, you can move title into an LLC later for a couple hundred bucks.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Also, I'm not sure how you're paying attention to it on the tax side, but the unit that you are living in's profit at sale is calculated differently than the other unit that you're renting out.Once you move out, that unit is officially available for rent so from that point forward, any profit gained at future sale will be calculated starting from that point and will be taxable.

If you're still looking for a CPA/Tax Strategist in California feel free connect.

Income would be from hunting dues and timber harvesting, expense would be conservation management, taxes, and the mortgage.

I am interested in utilizing space again for group meetings, workshops, and for clients who may still desire private space.  

You can also hold money for maintenance, capex, taxes, insurance, or other projected expenses.

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

Then utilize the same designs.