I will purpose choose the next few houses for the short term side, and keep the long term ones for more stable income. 

Keeping in mind your work schedule, choose something that fits your time availabilities and desires, not just one that gets you closer to the end goal.

I am a union ironworker making between $90,000 - $120,000 a year (depending on if I choose to work OT).

If you aren't familiar with the landscape in Philly I recommend working with local experts to choose and manage assets. 

I would personally choose the duplex/triplex.

Dealing with GC, choosing the layout, picking finishes, etc.. 

@Johnny McKeonThis reminds me of a line in a Chris Rock song..."

Trial and error is not for free and neither is an education and the bottom line is you will learn from both of them but you will need to choose which route you want to follow.

I agree to an extent, but this property is pretty nice, and in good shape so I want someone living there who wants to keep it that way by making sure problems get taken care of.If you are starting out and had to choose which side to live in which would you choose?

But just choosing a primary home that's out there now it significantly easier to find.There's other reasons too but we've seen this story before.