I think I'll go for it either way, because I'll self manage and repairs will be done up front, but running the numbers accounting for vacancy, repairs, and management, the cash flow is less than I anticipated.

I know there has to be a way, I just have to be smart about it and analyze everything and anticipate different outcomes and speed bumps it may throw at me. 

Any approximation on how much we should anticipate spending each month for utilities, snow plow, etc.5.) what are the must have items for a great rental property?

The property ended up appraising for exactly what we had anticipated (30k over our asking) and we delivered a cash flowing multi-unit property in an area where multi's are hard to come by. 

HI @Holly Litt - I would call the HOA manager directly to ask what the dues cover, if they are planning to address the issues you are seeing, and if they anticipate (or have the right to charge) any special assessments in the future. 

One of the major obstacles I was anticipating was the need for having the reserve account prefunded.

He's got a pretty sweet deal and I don't anticipate him wanting to move.

Peter Lynch astutely pointed out that much more money has been lost by people trying to anticipate corrections than has actually been lost in corrections.  

He said that it would be up to DOB and we would be able to challenge their determination but DOB would have the final word.But as you said any change would make the property worth less or require us to invest money that otherwise would not be needed and we did not anticipate investing into the building, such as closing windows, skylights, etc.

Tom Kairys it is in the ballpark but a couple of things to consider...What if you don't get the profit you were anticipating?