I went the owner occupied route on my first 3 homes.

You want to force the tenant out so you can occupy, which qualifies as an eviction.Talk to the tenant.

I would do you due diligence but I have seen others use it to purchase non -owner occupied properties.

In 15 years of management and 20 years of investing, I've never had a break-in on a vacant or occupied unit.

When I buy an occupied property, I introduce myself to the tenants on the day of closing; then, I inspect every unit within one week.

Often, they don't need to be moved in by the time of the appraisal, but if you have a signed lease, first month's rent receipt, and a receipt of the security deposit then the lender will often treat the property as occupied which can help increase your max loan amount in some cases.

My property is in 5th ward but in a more gentrified area with several new builds on the street that are occupied and 4 more being built on the street that are all for sale.

For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).

You can do less than 20% down (as low as 3.5-5%) if you intend to occupy the home for at least a year.2) There will be an HOA (homeowners association) which restricts rentals, so be sure to read the CC&Rs (governing documents) to ensure that your rental strategy is allowed, even if you intend to live there at first, eventually you'll be transitioning it to an investment property, so this will be important.

In Indianapolis C to B class neighborhoods I have rarely seen insulation upgraded on rentals especially doubles that have never been owner-occupied.  4th air gaps,  poorly fitting windows, and doors can be easily corrected with proper caulk and weatherstripping (usually).