The smallest real conversions tend to be single story commercial buildings of roughly 5,000 to 12,000 sf becoming four to ten units. A former dentist office, a small retail bay, a light industrial shed. At that size you're still looking at a total project cost in the low millions in most markets, because conversion construction is generally quoted per unit in six figures. A few hundred thousand dollars can be the equity in a project like that if you can find a lender for the rest, and it isn't the whole cost.
On your specific questions. Pre purchase feasibility usually means paying an architect for a test fit and a code review, plus sometimes a structural or mechanical engineer walk. Budget in the low tens of thousands for a small building, and treat it as money you may spend and then walk away, because that's often exactly what happens. Full design fees later run as a percentage of construction cost, commonly high single digits to low teens for a conversion.
Insurance during construction is builder's risk, which covers the building and materials while work is underway, plus a vacant building or vacancy endorsement, because a standard landlord policy generally excludes losses in an unoccupied building. You also want general liability, and your lender will name itself on the policy. Availability and pricing vary by state and by building, so get a broker who has written a conversion before.
You generally don't need a contractor license to own a project, you hire a licensed general contractor. Whether an owner can act as their own builder depends on your state's licensing rules, and some states restrict it sharply, so check your state board.
One thing that catches people at this size is the appraisal. A converted building with no rent history in a market with few comparables can appraise below cost, which changes how much a lender will actually fund.