The other is much lower but is a fixer upper that would probably require work that would bring the total cost to be $140,000 with the addition of the money to do repairs. 

Additionally, Lowe's allowed me to use their 10% moving coupon on the purchase and I saved another +$200.

Just thought I should provide some additional details.

But the contract itself has a stricter timeline.I'm not entirely sure what you are getting at.You say "Right, but if there is 17 day inspection period and Sellers/Agent provides TDS on day 17" ... all this does is give buyer additional time to cancel since buyer has a certain period of time from receipt of TDS to cancel.If your goal is to give seller additional time to cancel then giving them the TDS on day 17 will accomplish your goal.The inspection timer starts upon sellers acceptance of purchase contract.Also, I'd have to go back and read the contract, but I think if anything 'material' pops up whether from inspection, TDS or otherwise buyer gets additional time to either cancel or seller to fix.

Additionally tenants tend to destroy properties they live in resulting in additional renovation to sell. 

One additional snag is the size of the loan- 52-58k.

Could you qualify  for additional purchases if you sell and use that equity as a down payment to turn 1 rental into 3-4?

@Gary Dawson, there is a way to do that with exchange funds but it is an additional process called a reverse or reverse improvement exchange. 

Had I done this on my primary residence, I would of been stuck with aan additional $15k bill. 

The classification of multifamily properties is not set in stone.Some people look at it by Construction Year exclusively, and others weigh in the Property Conditions, Ammenities, etc.Here is a very general classification by construction year:Class A: 0-15 years oldClass B: 16-29 years oldClass C: 30+ years oldClass D: 30+ years old in high crime areas.To answer your specific question about section8 being a Class B or A, I’d say it is not likely.