I also know the market well from regular broker deals. 

Would the regular generic inspections be enough?

I have a secure job as well if needed to pick up the mortgage or other things if real estate market turns as well.

I am a computer geek by training, but I am interested in generating passive income so that my family can have financial security and the opportunity to travel and have adventures (without the day job). 

So while I'm saving and searching for the right property to have as my first investment, I've been doing tons of research and began listening to the bigger pockets podcast which led me here.I currently manage the service end of a new car dealership, but am looking toward the future and some day retirement and want a way to secure financial freedom.

Most landscaping companies will do one time services but they cost a lot more because they want you to sign up for a regular service plan.

However, I visit the area regularly.

With that risk in mind, isn't it easier and safer to invest in 100k houses and up and secure higher rents?

Continental and Secured are both good. 

Net income from Schedule C will result in both income tax and social security tax.