For the 2012 tax year, I had to repay (still paying), $6000, the outstanding balance of the 2008 HBC. 

The outstanding loan balance is considerably lower than market value.  

Scott,The eviction process varies from province to province, much like it does from state to state in the U.S.A.You can evict any time of year - the not being able to evict in the winter is an urban myth much like the unfounded belief that the power company cannot disconnect your electricity in the winter.The big issue with eviction in Toronto (TO) is the backlog in the system ... on top of a system which is tenant friendly.Down east in NB, we can file a Notice to Vacate the day after rent is due: the tenant has 7-days to cure (pay they outstanding balance) or 15-days to vacate.  

A future in which I can show my beautiful two year old daughter the value of hard work, all the while being adequately able to provide for her.I live in northern Virginia (DC suburbs), but have always had the mindset of working nationwide.

If they have outstanding utility bills, how will they be able to transfer all of the utilities back into their own name when they move in?

I understand the short sale (thanks), but I was thinking that there might be another way for the bank to reduce or dissolve the mortgage, without doing a short sale, but I guess not.When a relative of mine passed, there was an outstanding credit card debt.

:TheEPA  RRP rules are national, not local so it doesn't matter what city anyone lives in....Although the rules are federal laws so they are nationwide, location does matter because states and municipalities are allowed to be more strict than the federal regulations.

I've always struggled with why people do this - all property management software is not as expensive or complicated as yardi (and since you've invested in a MAC ... you can't use that expensive IE based software anyway).Many of the large operators/managers nationwide use software that is very much accessible to smaller sized landlords and they often pay PER PROPERTY - allowing you to grow into your portfolio in an organized fashion.I firmly believe to run a small or large portfolio - it's all in the software.

If you sell a property that still has outstanding debt, the tax bite is a littler higher.  

We pay the residential owners (by direct deposit is preferred) and send reports generally by the 15th of each month, provided all tenants have paid rents and there are no outstanding maintenance or utility bills.