If I buy a property for short term rental and do a cost segregation study to speed up depreciation, can I later decide to convert to a primary residence?

You could look into converting pre-tax money into a Roth IRA, purchase real estate and then all income and profits from sale, are tax-free in Roth IRA.

You might consider (Check with your tax professional) to convert any pre-tax funds, to a Roth IRA.

Maybe look into properties that have 3 or 4 bedrooms with 1.5 baths and the potential to convert the half bath to a full bathroom. 

What strategies can I implement to maximize rental income from my first property, which I intended to convert into two units ( Unit 1:Main house, Unit 2: Basement sun room) but cannot due to zoning restrictions? 

Hello. i'm under contract to purchase a duplex which I will convert to an STR. 

I wanted to get started in real estate investing and knew I could qualify for this home and convert the basement into a rental unit so it was the right house to start with.

That seems fair because they probably balance out to somewhere around $30-$40 an hour, which is a good wage for cleaning.If they don't like that, convert to paying them an hourly rate based on your market and pay them for the time required.

Alternatively, convert your first home into a short-term rental for higher cash flow if regulations allow.

You can defer tax payments to a later date.You may be able to convert the investment property into your primary residence to reduce your taxable net income.