He may just be a super successful 23 year old with no friends or family, but it sounds like a lot of potential for red flags. 

Being a landlord is a business it’s not a charity you’re not the Red Cross

I want to have everything I possibly can lined up to make my first actually step as smooth as possible.I know that’s kind of bold, but I’d rather take the chance!

@Gabriela Johnson I think there are a couple red flags.

You might not not want to risk having an illiquid investment in the red on your books.But either way, as @Russell Brazil and a few others have pointed out, crowd mentality is fear when there is blood in the streets and normal people cannot pull the trigger in a market flooded with vacant repos.

If you're plan is only to help others once in a while, you'll quickly start to realize that between membership dues (NAR, MLS and local Real Estate membership dues) not to mention monthly office desk fees (regardless of whether or not you work from home) and yearly fees associated with yearly 6 hours of required Continuing Education courses will keep you in the red and start to bleed you dry if you don't have enough business to cover these recurring costs.  

First, congratulations on taking such a bold first step: Door-knocking pre-foreclosures takes guts and persistence!

I am in no rush to make any bold moves or eager to get into something i can’t get out of.

This one immediately puts you in the red on the 1st unit.Are the property taxes accurate? 

Will doing this second deal raise any red flags for me or get me into trouble?