Picking a tenant for your investment property is a lot like dating.

You meet the person for the first time, and while you don’t know right away if this is “the one,” you surely know right away when this is NOT “the one.”

I’ve come across some pretty bizarre characters in the last few days…

My ad had been on Craigslist for less than an hour and I’d already received three phone calls.

As soon as I had placed my ad on Kijiji, I started to get innundated with emails as well.

The crack team of lawyers at Times Group Corporation insisted on including a clause that limited me from advertising my property for lease or sale on MLS, so I’ve been reduced to using traditional internet classified sites such as the much renowned Craigslist.

I need to find a tenant for September 1st, but I don’t get the keys to my new condo until August 28th, so I essentially have three days to locate my prospects, show them the unit, and get first & last months rent.

The issue I’m having now is that in order to find that “special someone,” I have to first weed out all the crap.

Again, it’s a lot like dating.

I once went out on a semi-blind-date with a girl that worked with my mother.  This girl came very highly reccomended (by my mother, which was my first mistake…), and so I thought to myself, “What have I got to lose?”

I remember sitting on a bench outside Starbucks on Queen Street in The Beaches, when all of a sudden I heard, “Hi…..David?”  There she stood before me, and after only a split-second of seeing this person for the first time, I knew…….”Nope.”

“Nope.”  That word alone has ended many relationships before they’ve ever been started, and while I’m the first one to suggest there is more to a person than their physical attractiveness, you really can’t move forward if there is no physical attraction at the onset.  So…..”Could this person be the one?”

“Nope.”

Suffice it to say, she and I still had dinner and went for a long walk on the beach (a cliche, no?), but that was more out of obligation than interest.

As I find myself trying to choose a tenant, I’m going through a similar process.

Literally five minutes ago, my phone rang, and it took me all of five seconds to think to myself, “Nope.”

I answered, “David Fleming,” and after what seemed like an eternal pause, a voice said, “Ummm…..hi, David Fleming.”  And that was it.

I had to solicit the rest of the conversation, “Can I help you?”

“Um, yeah,” the voice said.  “You have, um, like, that place at Rezen?”

“Yes, I do,” I said.

“Oh, cool.”  And then, another long pause as I sat baffled by silence.  “So, like, you’re not moving in right away, or what?”

Was this person looking for a roomate?  Or was she just completely clueless?

“No, I’m not moving in at all,” I said.  “The condo is available for lease on September 1st for a period of one year.”

There was another long pause, and I just assumed that the person on the phone was momentarily unavailable since it was her turn to hit the bong…

She soon revealed that she was a student at George Brown College, and if I ever needed more reason to say the word “Nope,” this was it.

I don’t want to rent my condo to a student, no way, no how.

Students are messy, irresponsible, lazy, care-free, immature, and unsophisticated.  I know this, because I used to be one (except for messy since my O.C.D. is ever-present).

What I would like is a young, single, business-professional who works long hours and will almost never be home.  Preferably somebody that works weekends as well or goes to see his/her significant other out of town every weekend.  Basically somebody who will pay me $1450/month to barely live there.

Last week I got a call from a man named “Roger.”

Roger was extremely well-spoken on the phone and sounded very intelligent.  He was succinct, asked all the right questions, and didn’t skirt around the issues.  But then he revealed his occupation: lawyer.

“Nope.”

That’s a little too sophisticated, too intelligent, and too professional.  I want somebody I can boss around a little bit and who feels “lucky” to be renting my condo.  I don’t want somebody with an excellent knowledge of the law who might decide to take me to the Ontario Rental Tribunal because I didn’t fix the broken washing machine fast enough.

Last night at about 11:30PM as I was eagerly awaiting the semi-finals in women’s Olympic Softball, my phone rang and it read “Private Number.”  I answered, and it was somebody asking about my condo for lease.

“Nope.”

If somebody lacks enought judgement to know not to call at 11:30PM on a Tuesday night, I have to wonder how else this person might lack judgement.  If it seems like a good idea to call a prospective landlord just before midnight, perhaps it also seems like a good idea to allow a close friend to start a marijuana grow-op inside the condo.

Am I being too picky?  I don’t think so.  If I don’t find somebody for September 1st, I can always find somebody for a mid-month rental on September 15th.  Sure, I might lose a half-month’s rent, but renting my condo to the wrong person person could provide headaches, monetary and otherwise.

Yesterday I received an email from a girl named “Shayna,” and right away I kinda liked her….in the professional sense, of course.  She said she was renting in the area and she abslolutely LOVED living near St. Lawrence Market, but her landlord is forcing her to leave with only thirty days notice.  She said she is a young, single, professional in the financial industry and she really wants to continue living in the same area.  We traded a couple of emails and I put her on the “maybe” list.

“Maybe.”

It’s like talking to somebody on the phone before you go on your first date, and you like the sound of their voice, their laugh, and the noteable lack of annoying quirks or catch-phrases.  This person could be “the one.”

But in the meantime, why not continue playing the field?

I’ve got a list of about ten “maybe’s” and I don’t even keep track of the “nope’s.”

Wait….are we talking about renting my condo, or dating?

Even I don’t know anymore…