Taxes 2800Insurance 1500Owner paid utilities: 2000 annuallyOnsite Coin op Laundry generates approx $100/month.Newer shingles on roof, vinyl siding 10 years old, all water heaters are less than 10 years old.One of the 3 bedroom apts needs new floor coverings and updates to bathroom (current tenant has been there for 20 years approx) will need to budget for repairs for when they move out eventually.Still budget for property mgmt although I will self manage for now.

I would also be careful not do this with a roof of multiple layers of shingles already on.  

Like in roofing there are so many parts. like flashing, felt, shingles, nails, ice and shield, drip edge, etc.   

A shingle roof here for a 2000 sq ft house would be about 10k.

.• Marble quartz countertops in kitchen & laundry• New handscraped espresso birch floors throughout• Wood-look ceramic tile in bath & laundry (and as backsplash behind the range)• New stainless steel appliances• Remote control LED lights under kitchen cabinets• Nest thermostat• New windows• New roof with architectural shingles• New horizontal cedar fence• New cedar deck• New custom exterior shutters• Generous setback from main road• Xeriscaping provides added privacy & noise reduction• Carport & enlarged parking pad for easy turnaround• Prewired for Google FiberRenovations took right at 100 days and cost approximately $60K (versus the 45 days and $40K the original GC promised us, but that's another story for another time).

Previous owner tore the tile off and put asphalt shingles on - which caused me to loose Historical designation.  

It's nearly impossible to blend in new shingles with old.

Part of the porch roof is falling down, and it needs new shingles on one section of the roof.

It has cedar shingles underneath 3 layers of asphalt, so it will need a tear off replacement.4) boiler is very old (1970s), but seems to work wellI suspect the first 3 items easily add up to $15k - 20k in near-term repairs.

If something happens over a period of time OR it was intentional or negligent on your part then it will probably not be covered by insurance.Mold does not happen suddenly - it is generally considered a maintenance issue.Fuel Oil tank listed above - if it leaks over time that is not sudden so... also a maintenance issue.A tree branch hangs over the roof and over time damages the shingles - not a sudden event so no covered.