I mean, hypothetically under what conditions/criteria would YOU finance someone's down payment as a debt partner?

You can always put in the contract 'purchase contingent of analysis of financials and physical inspection of property'. 

A bad financial decision can set us back a decade.

Settle the debt in full or partially. 

However in extreme cases you could be putting yourself at a larger financial risk.One important clause often missing or poorly written, from short investor contracts, is the defaults and remedies clause.

In this world of too much information and the need for attention to detail I personally like getting as much information as I can on any given subject; especially if it might impact or influence my personal financial situation which this does. 

I believe we are going to use a mix of the spreadsheet and quickbooks to keep track of our financials but as for paying contractors and vendors how do you separate each house?

Obviously I am on here to build a better financial future for myself and paying some one else rent is not a long term goal.  

I am currently also employed full-time as an IT contractor but, eventually, I want to be a real estate investor and landlord to achieve financial independence.

Currently learning, but I look at REI to give me the freedom to do the below things...1) Be Financially free2) Be the best husband and father I can be to my future children by spending as much time with them as I can!