I have some experience here, and my answer will be it depends. 

It all depends on what your requirement for cash flow is.

Investment property (not primary residence)So it depends on the type of financing.

You're looking for hesitation on how they speak of them as a person they did work/business with depending on a job or rental reference.3.)

For a smaller piece like that, not sure how creative you can get, but it all depends on what it's zoning is, access, proximity to other things, etc.  

Sometimes you dont have much of a middle ground depending on the demographics.

That will be tough to use your HELOCs together to get another loan because of your collective DTI so it will depend on that.

The idea of debt-free is that if a person is going to retire and has to completely depend on the income, they don't want a severe recession surprising them and causing them to default on the debt and losing the properties.In a normal world, I would do that as well.

That question depends on if you have enough other income to qualify.

It helps to make connections with your local flooring, tile, kitchen design studios depending on how high end you want to make your flip depending if it is in a HCOL neighborhood.