The problem was that I was making very little money as an instructor and need supplemental income.

I have a good chunk of money saved up, and want to know if I can supplement this saved up money with the money from my Roth IRA and 401k (from a company I interned at one summer but will no longer be working for.) as a down payment for this small multifamily home.

Your landlord insurance policy's limits can be supplemented by an umbrella policy with additional coverage.   

Eventually repeating the process until I can supplement my income. 

My goal is to add more sources of supplemental income and reach financial independence sooner.For the time being, while I am still learning, I would opt for a more passive investing strategy.

I understand that this is apples and oranges, but please hear me out and let me know your thoughts:I am thinking about switching back to a landlord policy and adding supplemental Bed and Breakfast General Liability Coverage through BiBerk (Berkshire Hathaway).

Just want to supplement my original post with the question of whether all good wholesale deals are found off market?

You'll also likely have trouble finding a realtor to take you looking at properties, but it might be worth becoming one yourself and supplementing your income that way.

Should I:Continue to save until I have enough saved.Cashout refi to supplement a downpayment or...Sell my home, have the downpayment and some extra savings afterwards?

Do you ask for additional bank statements, tax returns to see if the person has enough savings to supplement their Social Security benefits and qualify for 3X gross income?