I'm also contemplating investing in Northwest Indiana as I'm originally from Chicago and still have family and friends in the area.

It sounds at the surface like what you should be considering is another 1031 exchange to move into those new properties you are contemplating.

I am also contemplating on taking some carpentry classes at a local trade school so I can legitimately do some of the renovation work myself, and eventually become my own licensed general contractor. 

I am contemplating selling it and trading into a new place closer to where I live to shrink up my span of control.

I'm contemplating building my own house with the subs we use.

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.