This guy will always be a paint in your a$$ and your life will be less stressful without this bottom feeder.  

Decide which level of risk you're willing to take (based on your cash position, your personality, your confidence in your analytic skills, and your life goals), then compare properties until you find one with a risk-adjusted return that's HIGHER than your alternative investment options.  

I thought starting out with wholesaling would be a great way to do this (listened to several Wholesaling Inc Podcasts on this) and get comfortable with real life deal analysis/presentation, but then heard from a long time investor that it is unlikely with my time constraints that I would be able to put the time necessary into marketing and searching for good deals.

But as soon as you gain experience through life's ups and downs and get to the point where money isn't a problem anymore, you will get tired of the police calling you at 3:00 am because some dude decided to beat the crap out of his wife and threw her out in the snow and the cops want you to come down and open the door for them so they don't have to kick it in.

., in the meantime, if you DO have a cashed-up Investor who trusts you enough to buy whatever deal you present to them, hang onto them for dear life!

A life proof case for the iPhone? 

I had a good vibe from them too, and it was an absolutely miserable year of my life dealing with them.

A typical life cycle might be 5- 7 years from start to finish. 

I am 59 years old and have been in a related business my whole life.  

Finally, use all these numbers, including purchase price, repairs, rental income, expenses, and sales price or cash out refi after X number of years (you can play with these parameters) and calculate IRR on the series (can use the excel function to do this) ... this is your total return, over the life of the investment, including ALL sources of profit.