I am new to real estate investing and would love to learn from a mentor that was once in my shoes.

Enforcing a deed-in-lieu means the first position lender is stepping into the shoes of the homeowner and is subject to all other liens, including that of the private lender.

Or perhaps I should say that the technology has come a long way to enable an entrepreneur on a shoe-string budget to put out a book with an audio component!

You are (almost) living the dream life of my younger self - Mine would have included some white water, skiing and SCUBA - but enough of that So lets talk REI - If I were in your (rock climbing) shoes, here is what I would do - Use your 100k to pay cash for your first investment - you should easily be able to find a property to generate the $1,000 / mo with a $100,000 investment - Here in the houston area, we can get about $1,000 with just a bit more than $100,000 --- maybe $110,000 - $120,000  and that looks like a < 10year old home in a great neighborhood - but I'm sure you can get better returns with something less expensive in the midwest - Next I would just continue to enjoy your life and work occasionally while saving a bit of your income for the next purchase --- when you live below your means, it has a tendency to pile up pretty quick -- once you have a few thousand in passive income, you should be a more attractive applicant for financing to to accelerate your acquisition rate - The good news is that you are starting super young and it will be difficult to keep from acquiring a massive portfolio by the time you are at most people's "normal" retirement age-The other option (and less desirable in my opinion - although probably easier in the beginning) is to find someone with a good job/income, but zero money to invest (this forum has them coming out of the woodwork) and partner with them on the purchase --- use part of your $100,000 for down payments on several and keep a bit in reserve for emergencies--Whatever you do, you are way ahead of the masses- Enjoy the lifestyle and Happy Investing,jeff

I'm still working on getting my first property, so I'd like to be in your shoes buying another SFR.  

How much you want to "bet" on you being able to do that is up to you.What I would do in your shoes is look at the current (open) unit and ask yourself what it might cost to "spruce up" something with that layout, square feet, etc. 

If I was in your shoes I’d use a PM company for the first year (at least) as they understand the market (likely) better than you.

I noticed most listings on the usual's like Loopnet, showcase, CityFeet etc are all C class properties.

(I hate wearing shoes)

If I were in your shoes, I'd skip college, get a construction job or something that pays well, save as much as possible, and start investing ASAP.