Purchase price: $115,000 Cash invested: $42,000 Sale price: $168,000 Unfortunately, we bought this property as a buy and hold property, and our research led us to believe that this neighborhood was up and coming not in a bad area of Jacksonville.

Or like many small in businesses you raise cash from friends family and anyone else that knows loves and trusts you.The other thing I suggest is to make that $27,000 or $37000, or $50000 yourself over the next year. 

You will NEVER cash flow while living there but have a chance of cash flowing when you move out.

Yes, you can do a cash out refinance on the property to pull out some of your equity.

Can you either rent out your current property if there’s been little/no appreciation, or sell it tax free?

@Geoff Engel depending on what amount of available cash you are starting with and what you ultimately want to achieve will help determine your path.

Start with BiggerPockets Ultimate Beginners Guide (free).

If you don't have the extra cash, can you get creative with a private lender or partner stacked on bank debt? 

There are a bunch of investors from Calgary who are investing here as they find it more fertile grounds then there local market (So they tell me this)So the take home point is if you want to BRRRR in Winnipeg then you will find amazing deals with buildings that are burnt/plumbing/electrical work needed so you can get exempt from rent control and obtain the cash flow you want.

I can tell you that Rod Khleif's podcast is free.