HI Robert,I work with self employed and investors as a niche in lending. 

If I could give advice, it would be to try house hacking after finding full time employment.

  $425 to spray treat and bait termites.

I have told my current employer that I will be going from a five day work week to a three day because I need to invest more time in my dreams.  

All,I have a subject to deal locked up and I'm trying to figure out the best way to fund the $20K rehab.I have an IRA that was rolled over from my previous employers 401K with a balance of about $17K.  

Your strategy is buy and hold multi family homes (2-4 units) for the next 5-10 years to build cash flow to replace your present employer income.Do you: (A) put down payments on 4 - 5 different multi family homes and put a mortgage each one (B) buy one multi family home for cash, refi it out, pay off your HELOC on it and then roll into another home to continue this process or (C) have another idea?

But, using an independent agent will give you the flexibility to examine more than one carrier, so if you are a multi-disciplined investor a different company may have a better product for the various avenues of your investing.When it comes to contractors, unless they are under your employment directly, you should have no need to insure them.  

A lot really depends on the strategy being employed. 

Your day-to-day personal expenses are covered; you're free from credit card debt and other personal / consumer debts; you're saving in traditional retirement accounts, like a workplace 401k, up to your full employer match; you have a comfortable emergency fund.I'm assuming the real estate market, at this time, is "normal" (like 2014 or 2015).

I am self employed  and have been in the same line of business for 14 yrs.