Which is the safer bet?

It sounds like you banking on appreciation, your best bet is to make sure whatever you purchase it needs to cash flow out of the gate.

It's currently renting for $1500/ month but needs work and would aim to rent it for $1600- $1650, which is supported by comps in the area.I am currently renting a room on a month to month basis and need my own place, but have not found anything less than $1675/ month when all living expenses are accounted for (rent, utilities, internet).

I've looked on loopnet, mls, and other internet sites with no luck finding anything for sale in my area.  

Connect with me here or look me  up on the internet.  

I think your best bet is to show the condition of the property and that it is deteriorating and that the property will ultimately have no value to other creditors.

Jim Brewer, I understand the outskirts will be my best bet.

The first two lines read:(1) As used in this rule, "advertising" and "advertisement" include all forms of representation, promotion and solicitation disseminated in any manner and by any means for any purpose related to professional real estate activity, including, without limitation, advertising by mail; telephone, cellular telephone, and telephonic advertising; the Internet, E-mail, electronic bulletin board and other similar electronic systems; and business cards, signs, lawn signs, and billboards.(2) Advertising by a licensee, in process and in substance, must:Line two makes it seem like regulation is applied if you are advertising as any form of real estate professional.

If it's more urban infill then driving is probably your best bet.

For more reasonably priced flips, your best bet would be to pick up estate sales in condo buildings where the units haven't been updated in 20-30 years.