My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

While you're starting off, its not necessary.

Starting looking for opportunities last Fall and so far it's been terrible.

Breaking it down by room can make the process a lot easier.There are also some great pre-made checklists in Airbnb host groups and forums if you need a starting point.

Good job on getting started. 

Engage an investor-focused realtor/broker in your preferred market (this is not a residential realtor) and start 'tire kicking' the market and properties that fit your criteria.

Over the course of using Bigger Pockets I have had very degrees of opinions on who I should vote for concerning a post.When I first started using Bigger Pockets, I was too naïve to even think of voting for someone that took the time to answer one of my post.  

Quote from @Cade Antonucci: I am starting to grow my rental portfolio and am looking for online alternatives to hold security deposits.

Why not start thinking bigger?

@Cyndi Lees the thing that catches my eye in your post is that it would require quite a bit of work to get it started as a rental.