I understand you have to spend money to make money sometimes, but it can be a big challenge while going through a divorce. 

I should point out that I am extremely "challenged" when it comes to intricate investment/financial knowledge.Steve Vaughn said: "At Dow 26,000 I'd be dollar cost averaging out of equities honestly.

A few questions:1) what challenges have you experienced?

Been doing tons of research and it seems like New York can be a challenging area to getter started in as a newbie.

Since you are evaluating multiple out of state locations, this may be more challenging, but I bet you could find some folks here in the forums who can point you in the right direction. 

Me and my brother are just starting our Real Estate Business and we have an off market deal that a local investor and one of our realtors approached us with. 

Single family properties are a challenge to crack into but most investors have been focused on secondary suites and diversifying their risk. 

In seeking to kill two birds with one stone, I'd like to approach my landlord and offer to purchase the house from him.

He’s risking too, but usually you’re risking a heck of a lot more.Is there a chance to approach a seller directly?

Rather than choose 1 and hope they find a renter could I approach all of them and first one who finds me a qualified tenant gets the deal?