Good point about the maint. fees and repairs. Property tax is embedded into the mortgage for us.
I recall the maint. fees at our condo are ~$500/month and we just spent $10k on repairs + loss of 4 months rent due to sitting vacant while repairs were going on (another $7.5k). But to
@george__ 's earlier point, tenants paying rent for 10 years or so more than makes up for it these smaller short term losses.
$37k to $75k is a pretty big variance in price for a roof. 5500sqft is also a pretty damn big house! I grew up in a 4000sqft house and that was overkill for a family of 5.