(We ultimately moved back but the cost of holding the property unrented over 4 years would have been equivalent to the equity lost) Issues that impeded home purchases during the crash:  Credit dried up:  ie, the mortgage business transformed from handing out mortgages to anyone with 0% down to denying mortgages to people with 800 FICO scores. 

Unfortunately after reading more and more about  whether there is a Canadian equivalent to a 1031, I haven't found anything that would allow me to protect my capital gains until another investment property has been purchased.

You are already working the equivalent of 2 jobs and have 2 teenagers at home to raise and (hopefully) put through college in a few of years.Not a question of honor. 

I found it on the equivalent of craigslist on Puerto Rico.

He was making roughly $1k per month.During that same year, I bought a property in Clinton Hill, Brooklyn, but received break even cash flow.We spent roughly the same amount of money for our equivalent investments.Today, my Clinton Hill property cash flows over $3.5k per month.

After spending most of yesterday doing the virtual equivalent of throwing darts at a wall (looking at a map then checking prices in random areas within a three state or so radius) I ran across this: http://www.realtytrac.com/content/news-and-opinion/best-and-worst-markets-for-rental-returns-heat-map-8023 .

(Preferably, I'd want her to pay the equivalent of a security deposit divided into the rent, but that would come to about 100$ extra in rent, which she probably cannot afford) If she says no, she cant afford the extra $50, (thats the lowest I will go) then what course of action can I take?

@Caleb Godsey Your numbers are correct:However, you are missing CapEx reserves (5-10%) - consider Repairs and CapEx at 10% of rent, your cashflow gets cut in half:Make sure to account for all these expenses when evaluating an investment: 1) Mortgage2) Mortgage insurance (PMI or MIP) or FHA Risk base3) Property Taxes4) City Taxes5) HOA (Home Owner’s Association) Dues and Fees and Assessments6) Insurance Property Hazard InsuranceFlood InsuranceEarthquake InsuranceUmbrella Insurance7) Vacancy Rate (usually 8% - the equivalent to one month a year, or 5-6% if multifamily and/or if experienced, if not use 8%)8) Utilities (you’ll have some or all of these if your tenant is not covering them and/or during vacancy) Water § Sewer § GarbageElectricityNatural GasPropane9) General Maintenance (usually 5%) Upkeep § LandscapingSnow removalRepairsNew Appliances10) Capital Expenditures (usually 5%, higher is the property is old and obsolete, less if fully rehabbed and all mechanicals and roof are new)11) Property Management (8%, even if you self manage, your time still has value and there might be a time when you'll want to be completely hands off or you'll not be able to do it, vacation, retirement, etc.)

It looks like doing real estate deals with companies in Cape Coral is the equivalent of getting involved in deals suggested by emails from Nigeria!

I'm starting off with the equivalent of $50K, but this would only get me a mortgage of about $400K.