I would get rid of the word best in your first question because what I consider the best customer/tenant experience is going to be different from what you do.The best thing to do (to use that word) is sign up for a demo on both and I think they both offer a short trial period and really dive in and learn and figure out what one you like.I have used Propertyware, Buildium and Approlio (our current) and they are all fine and all suck, at least to our team and clients. 

My preference would be to get rid of him  as quickly as possible and suck up the loss if it sits vacant for a while.

If you don't the paint will suck into the drywall and be less glossy that the rest of the wall even if you apply 10 coats of paint.

Tell him you understand-- it SUCKS that he's been there for years, and has paid rent to a landlord that didn't do jack.

It sucks your parents don't support you now, but when you are successful, they'll remind you that they did and how much they were always behind you.  

@Adam BrittSounds like your wife needs to suck it up and find herself a decent job somewhere else .

Everybody fails or sucks at something too

In this business you can make some incredible income (i.e. follow Robert Kiyosaki and structure accordingly), meet some great resources and people (take a look at the answers you got here), and build something incredible with leverage.I went through my firs eviction last year - it sucked, consumed a lot of time and resources (especially emotionally... seemed all we did was talk about the jack@$$), and generally took my eye off the ball for a couple months.

And that would suck for me and many of my colleagues. 

Cast iron sucks.