Plenty of people (agents included) can come up with pie-in-the-sky ideas of how to change and improve a house, but few have a real understanding of what that work entails, what challenges will need to be overcome, and how long it will all take and what it will all cost. ...how did this agent know all this info?

Door to door prospecting is the most difficult type of sales prospecting because it’s (1) time consuming, (2) labor intensive and (3) entails a high number of face to face rejection.

I guess the only disadvantage with this option is the space issue.I also thought of just renting a bigger space while we increase our capital which may entail a longer time, but honestly I feel I'm already having tunnel vision and not being objective anymore.Any thoughts will be greatly appreciated, I'm sure I'm missing a ton of things with this picture and I'm not even sure if I am asking the right questions...Thanks in advance everyone!

The reason they stayed so long with us was because we had a good landlord/tenant relationship which entailed respect for each other, no matter what type of neighborhood they lived in or who they were.Landlording was and still is in my blood.  

And, if in the past you have set a pattern of repeatedly accepting late payments, the tenant may assert in court that this practice effectively established an agreement to a new, later, due date than whatever it may say on the lease or written Tenancy At Will. 

I have no idea why you assert they are more difficult to sell. 

There is a theory asserted by the Tax Court, but never followed directly, that a retirement account can be a disqualified person with respect to itself.

What areas are you looking at and when you say 30-40k rehab what does that entail?

You'll need to get creative and assertive.

I recently read Rich Dad, Poor Dad with my fiance and we got a strong desire to get in to real estate, not really knowing what exactly that would entail.