I would look at it in terms of whether you can afford a worst case scenario where you're covering the deductible and have a credit line or cash to front the re-build cost and getting reimbursed from insurance afterwards.

Overpromising and under-delivering in terms of expectations at times.

It certainly helps that you've done it, but I would maybe do one that is still in CA, but far so you can't go every day and see how that is and then inch out.On finding an agent, definitely not the way to go in terms of calling brokerages and asking for their top producing agent.

For a first time investor, I definitely recommend house hacking for most people as homeowner loans are by far the best in terms of rate and LTV. 

It is defined in terms of actions which would not be acceptable to any fair and honest man, or conduct which is monstrously harsh and shocking to the conscience.

What should I expect in terms of timelines, paperwork, or other administrative hurdles?

The tenant pool can be lower end in Winnipeg but if you invest in the right areas it will often qualify for CMHC financing in terms of affordability. 

Here are a few stats which should raise an eyebrow about Detroit $1 billion invested in more than 4,600 units of affordable housing over the past five years Job growth with more than 25,000 more Detroiters employed since 2014 A return to investment grade bond status for the first time since 2009Reductions in crime beating national trends, including the fewest homicides in 57 years Successfully hosting the largest ever NFL Draft at 775,000 people over three days In terms of starting out in Real Estate it also makes sense to invest in Detroit considering that the entry costs are low and if you plan to buy and hold, Section 8 makes for a great partner to insure steady rent payments.

In terms of scaling to three to four multi-family properties, you could really start using the equity that you do have to your advantage. 

It's worth comparing terms between your current lender and others to see who offers the best deal in terms of rates and fees.Purchasing a Property: Whether you purchase through regular listings, an agent, or an auction depends on your risk tolerance and expertise.