The area isn't a high net worth market where they need to see you in designer clothes before you are taken as a serious buyer.  

Unless there is an instant family on the way and you absolutely need more space (even with a new family a 2-bdrm cottage is sufficient - babies do not need much space in the first year).Why not stick it out in the present house for another 1-2 (or maybe 3-4 when your finance has finished university) years and pay down more of your debt (student loans and mortgage) to put yourself into a stronger position to acquire investment properties.In the interim, you could further educate yourself on real estate and start to narrow the gap on selecting the type of investing that best fits your lifestyle and ambitions.

I came from family owned horizontal projects, I hate starting from scratch, but baby steps to financial freedom, we need to start somewhere. :)

If I need a respray within 6 months, it's only $75 (not bad).I have a feeling I am going to run into a language barrier issue- one side is Hispanic and speak very little English, and there are quite a few things that the tenants have to do to prepare for tomorrow (dry all their clothes, vacuum, etc.) and I'm worried they won't listen to my wife and the treatments will be useless.

They once offered up the basement for furniture storage for a charity drive... and also used the washing machine to wash about 20 loads of clothing they were going to donate. 

During my 28 years of police patrol work, I can't tell you the thousands of times that I have witnessed great "wailing and gnashing of teeth" as soon to be displaced family members begin to shout, rip their own clothing, beat on their chests and call out the names of deceased family members in an effort to avail a heavenly intercession to prevent being "put out." 

That's the whole point.I've bought many properties and probates in particular whereby occupant is an heir, a relative, a friend of decedent, ex-partner/boyfriend/girlfriend and grand child's baby daddy and biker buddies. 

Yesterday I went to the house and there were clothes and boxes inside the house. 

The lending laws have changed since then.That's the reason many baby-boomer's have a mindset of get your loan paid off as fast as possible because their parents went through the Depression and knew what it was like to have a loan called for no reason.

I hope I am a little more mature now and can set baby step goals which will hopefully lead to closing on a deal in the next couple of months.