For example, if ma and pa have owned the property you are looking to purchase for the last 20 years, the property could easily be assessed far below the market value.  

The concerns about the age and condition of the building are unfounded as they are easily remediated with minimal time or capital.The issue about parking is also strange given that it is an urban neighborhood and it is quite common.

Do a few deals. then once you can easily do one deal a month , worry about checking accounts, llcs, etc.

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That's how I'd interpret their requests.If the NY market is as much of a seller's market as it is in MA, you're not in the driver's seat - especially if they already have a better offer.If the numbers no longer make sense with those repairs, just drop it and move on.

Problem is that even those of us who play by the rules (I pay ONLY by check, send out 1099's at year end, etc) and know the rules of employee vs contractor can easily get caught up and can get whacked hard with fines, interest, etc. 

I have purchased a smaller house for my disabled brother, which he can easily manage to rent from me, with me providing all the upkeep and maintenance on the house(which will be a rental for him).

If you buy an old turd of a property that has not been recently overhauled and updated....plumbing, electric, roof etc...not just paint and carpet....then you could easily exceed 50%.  

Someone can easily sell you a mispriced (it doesn't matter if it's intentional or their own error) property and you'll be stuck with it.

If the current manager won (results wise), he keeps his job and above market compensation after bonuses.If the new manager won, he replaced the current one.He found this to be a highly effective way of keeping his pay per click managers highly motivated  to continue optimizing the campaigns to the best of their abilities.This is more easily done in the online world, but I wonder if such a competitive incentivization scheme would work between property managers as well.