I don't want to cap my account at $20,000 if I know a roof costs $25,000, but I also don't want to go up to $100,000 knowing that if every CapEx item came up the same year it would only cost me $75,000.

All they did was cosmetic and patched the roof.

Due for a new roof.

Construction materials: Frame, no basement, roof: asphalt shingles, Floor: Carpet on stairs and bedrooms, LVP: Kitchen and living room.

As many others have mentioned, it does seem very likely that an adequate walk-through/turn was done by the PM company as well as it may be possible that they also have a poor contractor that is not fully resolving issues like leaks the first time around. 

Otherwise they will continue to pay yearly taxes and maintenance costs, and not be able to foreclose the property as it will sit here leaking and falling apart and the mold continuing to spread.

We then spent around $30,000 out of pocket on renovations, including repairing the roof, upgrading the electric panel, installing new HVAC, and putting in a new kitchen.After completing the work, we refinanced with LendingOne using a 30-year fixed-rate DSCR product at around 7%, which resulted in a net cash-out of approximately $15,000.A couple of things to note:I'm out of pocket on this property for around $40,000 ($25k down, $30k rehab, minus $15k recaptured).I'm thrilled with this amount since it's far less than our "normal" 25% down strategy would require based on the higher value.The property appraised for $330,000 after the renovations.The key point for me is that this property is now netting around $800/month in cash flow.

What is the going rice for new roof for 1500 sq feet house in Montgomery? 

This is just the normal operating costs, never mind the big things that come up occasionally with capex like when you have to replace a major component (furnace, water heater, sewer line, driveway, steps, deck, windows, roof, doors, siding, landscaping, etc,) and it costs $10-20k.

The maintenance differential between a single-family and a two-family is twice the mechanicals, but the same amount of roof, exterior, etc.