This is called delayed financing.

Is there anything I need to do, or be aware of when buying an occupied property with section 8 tenants?

There are lenders who will finance land but leverage will be lower.

You're right to think about the tax implications of paying for the roof before owning the property.

I recently purchased a rental property and discovered it needs more extensive repairs than I originally anticipated.

I am considering whether asking  the bank for a loan over the property to use this capital to buy another fix -flip property   Or to sell the property,  ( maybe  wholesaling because closings costs would be expensive leaving no profit left)  I am here to read your ideas on this.

Once you stabilize and raise the rents it would be the hope that the property would appraise for more and the owner would refi and get back significant returns.

I have seen multiple properties with low asking prices and sufficient rental income to cover the note.

My hope is to finance 50% of the purchase.

If you have a property manager handling it for you, pass it along to the Tenant at cost of the Workman plus the markup of the property manager, whatever amount that is.Spackle is cheap, but paint can get costly especially if two coats are required.