Some people use real estate to boost their quality of life by having a second home loan on an Airbnb.

I have a family friend in dire straights, her husband died a few years ago and her son and her self have some mental issues, they are no longer working and she collects about 500$ in social security.

I had my mental estimates of what things would cost, mainly cost of the product and general labor costs if I used Home Depot or Lowe's, and had that as a round about idea going into the first rehab.

And I had the same mentality you did with this statement on your post "I'd like to find a property that I can fix up cosmetically to raise the value of the home & provide me with cash flow in order to start saving for my next investment." 

We've been sticking close to major commercial/retail sections and also employing a creative strategy called "padsplit" to boost income further.

So id say I'm mentally aware of the whole process and what's to come, but naturally I don't have actual experience until I start and that's never changing unless I do.   

That's the beauty of the REI world: lone wolf or pack mentality, there is a lane for you. 

Deliberately have a few challenges in your screening process - it will weed out "entitlement mentality" problems4) Allow payment plans, but create system to track when payments due, so they don't keep falling further behind You will need to call them on due dates or they will fall further behind Be prepared to give a strong NO when asked if you will change rent due dates to "make it easier" for tenants to pay rent based upon their SSI or paycheck dates.

My offers have all been BELOW asking but my mentality is slowly shifting.

This will decrease your overall living expenses which will be a major boost for your financial life.The only issue you may have with acquiring these two properties back to back is if you plan to go conventional on the loans.