EX: I ran a few real estate ads targeting real estate agents on FB. as a test since I never did an ads before.

They're pretty organized, but expect annual inspections and some extra paperwork. 

That way you wouldn't need an extra policy.

I won't go with the riskiest opportunistic strategies, and will stick to core and core plus mostly with some value-added.

If so, am I selling/transferring the title or am I just adding the entity to the title?

If your average heating bill is $150, you may not collect enough in the winter months when the bill reaches $225 but you'll collect extra in the summer when it drops to $65.

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

-A water heater issue resulted in repeated mismanagement—confusing unit assignments—leading to extra costs to fix the same issue 3 times and on each occasion "more fixes" needed to the water heaters that I plumber said was needed.

You'll want to have an insurance agent familiar with rentals since a lot of the extras on your coverage that you will want, the average insurance agent won't know to give you. 

Compliance items such as adding smoke detectors, hand rails, fire resistant garage entry-door and new stairs outside.