I am investor looking to buy the first rental property that I do not live in, and I have been contemplating getting a real estate license.

I've been contemplating flipping but know eventually buy/hold is where it will be at for me.  

There is now I believe a seven year contemplation rule (up from 2 years) for any transfer in contemplation of death or incapacitation.

I've done it with tax deed properties during the redemption period, but never contemplated just finding a vacant house and taking over.  

This was more prevalent in the go-go days prior to 2008, but it still goes on today as well.There are actually, 8 or 9 criteria that the IRS uses to determine who is a dealer and there is case law on the subject going back to the 1960s, so a simple answer may not be the correct answer.If you contemplate doing development, you should have on your team a land development attorney as well as a CPA versed in dealer issues. 

Here are questions I ask myself all at once in the half-second I contemplate not going to any meetup: Am I going to have to walk in the dark?

To get into that path of progress, you are going to have to get a feel to see what areas are set for improvement by talking to locals, surveying the landscape and trends, contemplating potential new transit lines or nearby large developments, etc...

I have been contemplating whether or not to claim all my expenses.

But omniscience isn't necessary; you only need to understand the actions you undertake.If you instead focus on the prospective price change of a contemplated purchase, you are speculating.

I thought this was a pretty smart idea on his part and after some contemplation came-up with the grand idea of buying my own duplex but with the other side paying ALL of my expenses and hopefully more.There was a few problems with this though:1.