Also, and most importantly, it will supplement his current monthly passive 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.

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. 

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. 

I'm essentially coming from square 1.I'm later in my career, and am currently thinking of notes in terms of providing diversity in my portfolio, supplemental income, and providing better returns than the market.   

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. 

I don't want a bunch of rental properties, just enough to nicely supplement my other income.

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!!

One downside is it's not so great with taxes (reconciliation + depreciation) and I supplement with an accountant who uses quickbooks. 

Therefore I've been looking into pursuing the world of Wholesaling to supplement my income.