I am looking to purchase additional properties to rent, to initially supplement my income.

John Hickey hey John thanks for the kind words and yes I worked in college so far but I am planning on getting an actual on the books job to supplement the loans I would need.

I would not rent the unit for $1,000 a month if you have that much equity to use, you could use that money to make you way more then your ever going to make renting if your looking to supplement income.I guess the real question is to figure out what you need to bring in monthly to live the way you want and once you have that number then you can move forward. 

1 year goal: purchase 2 investment properties5 year goal: generate enough cash flow to be able to work for myself by supplementing my income with flips10 year goal: invest in commercial and multi-family properties...and let other people do the heavy lifting!!

Insurance isn't crazy at all - I added a small umbrella plan to supplement AirB and B's policy.Aesthetic, ability to host small families (3-4 people comfortably) and marketing will be key/everything in Levenworth.And yes, a local neighbor, or responsible HS or college kid who wants to make $20/flip is key. 

Owning your own home can give you leverage to purchase your next property.I know some real estate investors that prefer to rent their primary residence and enjoy the freedom to move around more, supplemented by income from rental properties. 

Here is a list of great books to supplement the forums & the podcast: The Best Real Estate Books Ever If you have any questions, feel free to ask.

I would prefer to have residual income to supplement my retirement and be able to pay back all the years my family sacrificed for me during my service - all I want is to be able to actually retire when my military career is done.

Private money lenders do not advertise . its not their business they just have excess cash and want to make a few loans for their IRA or supplement their income.. 

My goal was always to have them paid off quick and have 10-12k/month in passive income from 10 properties to help supplement my 401k.