How much weight/consideration should go into it when making a purchase.

The harder the list is to come by the better your chances of securing a deal.

I have been reading but still don't have a definite plan in place to secure that first contract to flip.

I would have contracts in place to protect the interests of all parties so everyone is safe, secure and profitable.

I do individual loans, secured by individual properties.  

The owner is more likely to just delay the foreclosure and in some area it could take years meanwhile the owner could be staying with family renting out the place to pocket the cash off the books and than a few years later the foreclosure finishes and he could get bumped into section 8 (depending on location) with the bill 100% footed by his social security or workman comp assuming they are older or just lost there job because of an injury.... or no matter what the age maybe there just a deadbeat and will burn the place down and let the insurance deal with it...

I am interested in real estate to widen my portfolioto have a secure retirement.

The term "high yield" is much like "Lose Weight Today" how much depends on the eye of the beholder.  

Now that is some serious weight.

I was able to secure funding through a hard money lender so I'm confident I can close in 3 weeks if we can make a deal.