Buying Rentals While Still Renting Myself? Yes or No?

[Jack Barkow]

Hello BP.  I recently moved to the Chicagoland area and have been looking at getting into the rental market for some time now.  Since I'm confident that I will be here somewhat more long term than where I previously lived I would like to start to accrue rental properties.

The question is that since I was moving here I did not immediately buy a place so I'm wondering if it wouldn't be the worst thing to go ahead and start to accrue some rental properties while I'm still renting an apartment myself.  The way i see it is that it would be far easier to live in the place that I'm renting out (duplex/triplex/multiplex), but that it also shouldn't really make much of a difference in the scheme of things since cash flow is cash flow and I can throw the profits at my current rent payments and still technically manage to live for free/reduced cost.  Then, if a vacancy comes about around the time that my current lease expires move in or look to buy another property around that time that has at least one vacancy.  I don't want to miss out on the opportunity cost of just saving up money for another year (Realistically 6-7 months since I'm not buying something today).

What would you recommend that I do in this situation?