One option is to keep them all and use the rent to supplement my pension. 

Your peer and mentor network, and RE literature options, should be an occasional supplement - not a crutch.

To begin with, I am not seeking cash flow to supplement my own cash flow, but to be reinvested towards future property purchases. 2) Long term I would really seek to own a fairly large portfolio of rental properties (Single and Multi-Family) that will initially replace what would be my wife's income and then potentially mine down the road. 

I'd rather leave the properties that need a lot of work to the house flippers (and even those seem to be selling at 177k), I'd prefer to not start out with a huge monthly expense while coaxing a house into positive cash flow with supplemental money, and putting half or more down will make getting started like trying to drive with the breaks on. 

A general Business Plan can be supplemental material that helps to communicate your overall strategy, marketing plan, neighborhoods of interest,  company makeup, etc. 

These purchases are often times part of a investors retirement plan, supplemental income, etc. 

Her husband had to pick up an additional job to supplement the income. 

http://www.lowes.com/cd_Special+Offers_381632314_Jon, I was in Lowes the other day and the sign stopped me in my tracks, selected carpet and they supplement the layer's labor from the deal, that money comes from the higher priced goods, not really a deal in my area as I can get my own carpet layer.

Know your ag requirements around there....do the cattle need 1-5-10-50 acres around there to survive without supplemental feed. 

If you are wanting to supplement your income with rental income more immediately then I think this would be the way to go.