So it shouldn't be too difficult to get him to play ball as long as you let him know you're not wasting his time and gives him business for the deals that will work.

Originally posted by @Wes Brand:50% makes sense to me -- you left out buyer/seller agent commissions (6%+), and carrying costs for 6 months. 

Taxes will play such a small role in your two different scenarios that they should be a minor factor to consider.When asking about taxes, better questions would be:1) What asset class yields the best tax advantages?

From there, you can determine what components are priority, and how much of a factor location will/should play into that.

I am brand new to investing, I've been doing lots of research and was just wondering if anyone could lend some advice for someone just starting out.  

I also have a meetup once a month in Yonkers and we play the rich dad cash flow game.

All of that does play a part however the question is where do you want to start as far as do you want to just do wholesale, fix and flip, etc. where is it that you want to start?

At the time, my two oldest boys were playing middle school football, so I talked to a handful of dads i was friends with and convinced them to look at this potential investment opportunity.

I'm brand new to REI and I want to use private money to do rehabs and flips in the Tri Cities, TN area.  

Just put simply, all cash means no contingencies and in NYC that's the way the game is played.