If I were you keeping the property as 4 units and renting out bonus unit under the radar may be your best option especially if you plan to refi or do HELOC while occupying. 

Hi Jennifer - Am planning to invest in the Cincinnati OH area looking on the east side.

A good tax accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in business taxation, financial planning and tax planning.I would also recommend looking for a accountant willing to work with you throughout the year.

Edit: I don't plan on doing any of the work myself aside from the most basic of things.

.: Decided to try to use Obie on a new acquisition because my traditional insurance doesn’t do new policies in California and the insurance agent recommended by my loan officer just wasn’t working fast enough (CA Fair Plan seems to be at fault) to meet our closing calendar. 

The initial plan is a 1200 sf build out with plans to expand back away from the cliff later as finances and interest rates are more favorable.

In this manual (which I assume could be modified to provide to tenants) I include all the financing information (which you would not include for tenants) bank accounts, mortgage accounts, payment information, and mortgage payoff), a list of the contractors, what each contractor does, a list of upcoming planned or necessary repairs, and a copy of all leases associated with the property.

I am drafting the lease and planning to take it with me to closing, where we will be executing the document.

Can I pay property taxes in January that are due now, then deduct them as well as next years that I will (plan to, anyway) pay in December of next year?

If you are a buy and hold investor and have no plan to force equity that is a different story.