The downside to this would be delays in closing or even worse, the deal not closing at all.I recommend waiting until you own it to ensure your able to hit promised timelines 

Poker players call it rat holing.Everyone of your choices is incredibly valid and incredibly wrong depending on the market.  10 years is probably way into another market. 

I have been employing the tactic of using the listing agent for the offers I've made thus far (for the reasons of double commission), but I would probably be better suited to use an agent myself to ask these questions and ensure I'm protected.

Before one puts a nail in a stud or even puts an offer in on a property, they need to understand who are the key players in a Real Estate Investing team.

If you don't, diversification will ensure you never have enough to where diversification makes sense. 

@Philissa Gilliard Ensure you think through your wholesaling goals and have your site strategically built to support these.

On top of that ensure you have enough reserves to handle anything that comes your way.

Well worth it in the long run to ensure you don't end up stuck in a deal that doesn't work, or even just to avoid wasting 2-3 weeks in waiting and contingency periods on a property that you won't buy. 

This will allow you to engage with people in your market as well as people interested in your area(s) of expertise.I also like putting in searches on the Bigger Pockets search bar for "Queens, New York" to see who are some of the local players I haven't yet connected with.A few other things; post regularly on these forums, comment on blog posts, try to make a few new connections each week.

I do agree that starting with one of the bigger players is probably going to be the best way to learn and grow your business initially.