Right now, I'm thinking about retirement down the road and want to try a buy and hold approach to hopefully build up some income for when I retire.  

Your goal is aggressive and I like it but be realistic....We all dream of retiring after just 8 years of investing but that's not statistically likely.

I was thinking of establishing the LLC, opening a business bank account and depositing $20k and using those funds to get a loan to purchase a home then rent it out, show that as revenue to a bank, and proceed to buy another home, and slowly rinse repeat with cash flow or breaking even with the long term goal being that the mortgages get paid off in 15 years to where eventually the renters go from paying down the mortgages to paying for my early retirement.  

He self manages and is retiring. 

With the new income from the business I was able to retire from my job and pursue investing, I know it will be much harder now to build my portfolio, but with plenty of hard work and the educational opportunities and creativity of this community I will meet my goals.

I have started off as a buy and hold investor because I like the idea of passive income for retirement (I'm 55 and looking to retire in about 3 years).

Also, the property is not secured by the 401k funds. https://www.irs.gov/Retirement-Plans/Retirement-Pl...

That is my long term goal to be able to retire 17 years before the average person. 

Disclaimer/Disclosure: I should have added this eight months ago, but have been busy doing real estate, in spite of being ‘retired’.

However, he is now in a position where he has the cash, but not the deal to invest it in and get the $50k or $60k annual return he needs to retire.