The cost of starting a site is often minimal, and every dollar of incremental income is a large fraction of your start-up costs.

I consider that a competitive advantage that I will have in the long run.

In my area there are literally hundreds of similar ads posted, as this is a highly competitive market!

I think allowing pets are a huge competitive advantage.

Actually most first time investors form an LLC with an experienced one to qualify for competitive loans.

If you are looking on market, you really just have to be quick to jump on a deal in the area since everything is pretty competitive still and it is kind of difficult to find cash flowing deals listed on the MLS. 

Even though banks only had a fractional reserve requirement of 10-15% before, lending without requiring any reserve whatsoever is a very scary proposition. 

You're also being overly cautious, which is understandable but also inefficient use of time. if the market is competitive then speed is the key, he's trying to tell you to go fast and you're resisting, do you have his best interest in mind?

I am unsure if I should invest locally (within NYC) given that it is super competitive and overpriced.

Once the work is complete you should then get it quoted with a carrier that will be more competitive on the pricing since all the risk will be mitigated at that point.