Might be tough from area to area, but I typically find that homes built before 1950 that were converted from single to multi family are 9 times out of ten - a full gut rehab and way too expensive for first timers.

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? 

Selling and dropping the equity into an index fund is a lower-maintenance option, but you’d be locking in your gains at a relatively stagnant point in the market.Given your low interest rate and the potential for rents to inch up, renting could be a reasonable play.

The first interactions are critical,  every inch you give, you will never get back.

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.

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