ok,

1. repair AC: check what needs to be repaired, if just add R12, it only costs $100-200.

to get a new AC, probably 3,000.
check if you need to change furnace , if so, you will be added another 2-3000.

2. easy and cheap. for rental, I would go with cheap (not the cheapest) one. cost $300 each.

3. do not know until you have figure: how long? how big the house?

4. do not know what to be repaired.

5. roof: what kind of roof materials? repaint (cost $1000-$1500), shingles (cost 2x, 3x), tiles (cost ??)

If you do not say specific, it is hard to tell.

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