Some of this will be about your own confidence in how wisely you use that money, because of course taking out debt (and with the extra costs associated with it) can be dangerous, but if you're smart about it, taking that mortgage out might be the reason you're able to succeed later.

Which it very well may be.Every squirrel within a 500 yard radius is now in significant danger. 

When your tenant has been consistently late in rent and is clearly in danger of eventually being served an eviction notice, they said you should take them out to coffee and warn them of the dangers of eviction, and suggest they move out.In general, and here in Portland, OR in particular, that seems like asking for a lawsuit.

Two amateurs would be dangerous.

The first few deals are the most dangerous as you are learning the ropes.

Might as well get ahead of the curve in case for whatever reason you would need to go in front of a judge- OR more importantly, if your place does in fact pose a lead danger so you can do the right thing and address to take care of your little baby tenant!

We must remember that counting on appreciation or cash flow in the future is a dangerous game to play.

That's potentially dangerous for that mortgage broker to have done!

Curious if anyone has deployed this strategy where you list the same property as two distinct listings on a platform like Airbnb or VRBO?

The danger is if someone in the chain doesn't perform, lots of people are involved and lawsuits could get started if it didn't go properly.