The pros of condo rentals is that you don't have to handle/pay for exterior maintenance or lawn care (outside of your dues). 

Maybe I am missing something. 2 loans, insurance, taxes, maintenance. looks thin to me.

From what I understand of CT law, the tenant must report the maintenance issue and then give the Landlord 15 days to repair before the tenant can withhold rent.

House hacking allows you to gain first hand experience in land lording, property maintenance, screening tenants, etc.

I'm sorry to hear this.Contact a local attorney who handles L/T routinely for advice and do what they say.You can likely file an Unlawful Detainer to have her removed.But you might also try contacting her Housing Authority caseworker, posting a notice & attempting to meet with her in person and being extremely empathetic about what she's going through. 

I purchased a few properties that were sold with some deffered maintenance issues "baked in". 

Not aware of a PMC doing something like this.There are Property Maintenance companies out there though.

.· Neglect maintenance which leads to bigger and more expensive repairs down the road.

I bought a few properties with some deffered maintenance issues handed down from the previous owner.How do you all attack it? 

All the time.Over 80% of lease option deals fall apart and the owner takes the property back with deferred maintenance, unpaid rent, etc.