I’m basing that more on things like W2’s being issued by a business versus what was reported by the person who received it - but I imagine it extends to all types of transactions.you are flirting with danger though.  

Depending on how much experience you have that's related to the job, you might not need to wait.

But even that depend what your end goal is.

What a cost segregation study does is it analyzes a property and breaks out the depreciable basis of the property to more than just building and land.It will try to identify assets that are eligible for 5, 7 or 15 year asset lifes which would be eligible for bonus depreciation.Whether a cost segregation study will help you depends on your tax situation.High level, it will help you in two situations1) Your rental property is active and you can offset the losses against other forms of income.2) You have a lot of passive income and you want to increase your passive losses to offset your passive income.Best of luck

NY state website has a broken link to an opinion about what constitutes "doing business" in the state. 

Find property in a good location, at a good price, and at a good point in the real estate and business cycle, with the most leverage you can get, ie. the lowest down payment are some of the keys to success, whether its residential real estate or commercial.and don't beat yourself up when you screw up, which you of course will, many times.

It has proven to be more difficult to set up than expected mainly because of having to use a third party company for a physical business address1.

Obviously there's a lot I don't know about your deal, but using napkin math and your figures, Id go for it - I think $1600-1800/month is realistic depending on the area at that valuation (just guesstimating the neighborhood quality based on ARV).

So I met with a gentleman yesterday who is an Executive and Business Coach.

If you want to get into the flipping business, then give it some priority and don't treat it like others treat their hobbies.