My parents live in Stockbridge so I come down occasionally which is why I'm familiar.

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’ll ask you this, if someone offers you to work every saturday at $30/hr for 8 hrs, and there is one who pays you $350 for 8 hrs on occasional saturdays meaning it is a hit and miss every saturday, which one will you pick?

I'm buying distressed foreclosures in north nj, fixing and renting, with an occasional flip.

With an AHS warranty, for the most part you'll have a steady premium, then the occasional extra $75-$100 service call fee to fix issues (except the above A/C example), instead of the potential unexpected replacement of appliances which can cost more in a given month/year, but over the course of several years will likely work out cheaper.

Perhaps the employees and an occasional customer might use the service. 

occasionally that means doing some of the maint. myself.As far as getting into flipping.

Next, from what you said, it's my belief that you're already on the right track.Ann Bellamy pretty much shares my view - I have experienced that it's best to pretty much never sell anything, although there are a few properties that after years, just didn't fit the long term plan, so an occasional sale maaaaaaaaaaay be ok.Next, she said "buy more properties faster."

Occasionally I’ll talk to someone that thinks they want to do it but they really just want a manager or to not get in the business at all.

My gift....... being a good LL and taking care of the property....responding quickly and efficiently to issues that come up.... providing maintenance as needed and occasionally updating or upgrading the unit as I see fit.... that's it.My job is to offer a good, clean, well maintained unit...... not have you "like" me because I bought you a gift.