For instance, where to get appropriate paperwork? 

It depends on your overall tax situation for the year, for instance on your occupation listed as "contractor" which can mean a lot of different things.Of course you're "a little cloudy" because this whole thing is far more complicated than my one paragraph above.

Ie does the path of progress look to be heading that way?

If the price is low enough to cash flow then it’s probably in the barren desert, somewhere you won’t be able to afford fire insurance, or somewhere filled with meth heads.

For instance, in the event that you need to make an offer over the listing price to win the deal, would the financial terms suggested in your Contract to Buy be strong enough to convince the Seller's Agent and Sellers that you will be able to close? 

It's been a busy few months working our normal 9-5's and then heading up to the cabin to work on the weekends.

I’m just trying to get my head around buying a dumpy old house and a trailer for $150k.

When you head east past Bowmanville the demand and quality of homes drop dramatically.

I'm heading to AZ next week to drive-for-dollars and find my first BRRRR property.

If for instance you are leaving a much larger home and down sizing on the next home, this can be a red flag.