If anyone tells you that you can get 15% cash-on-cash it's either a scam or ultra high risk. 

@Sakib KhanRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Those qualities can be the difference between closing a deal and walking away empty-handed.What about you?

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

So quality of tenant is irrelevant as accidents can happen.So most of your post demonstrates that you did not really think about it.  

DOM can be minimized by a number of different factors including the quality of marketing, rent price, availability to show. 

First off, all high skill requiring items let's remove those.

-------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

He has been alongside me on the other deals so I’d like to give him equity/skin in the game and I don’t know how else to do itQuote from @Basit Siddiqi: Getting a property with a partner / friend will not help you from getting hosed on taxes.I wouldn't move forward - You mentioned beng a high income earner so your hourly rate is very high.

If we're going to just talk in hypotheticals, of course anything is probably possible anywhere but highly unlikely.