All that said, property management is tough and I would absolutely read reviews. 

The simple answer is that in a tough market to find deals you need to look at more deals in order to get one.

MA is a tough state for evictions and you may need money for legal fees.  

As much as the CT market is tough, the NY market can be even tougher! 

If you do it right, it will prove the benefit and he will be more likely to let you handle the rest.I would also consider educating him on tax liens and why he needs to get those paid off ASAP. 

I own a couple and the cash flow is tough to beat.

It has been a great learning experience so far but has been tough since we both have wives and small children and are working on the house on nights and weekends. 

The value of a good tenant is sometimes worth putting up with certain, lets call them "quirks", but those conditions are pretty tough.

This is going to be a tough question to answer accurately with no info. 

HOA's can be tough as they limit your use of the property.