ability to comfortably rent out the basement for 1200 per month Lessons learned?

I would be comfortable paying $2,000/mo with Mortgage, PMI, Taxes, etc... 

With things growing, I really want to leave my 9-5 job to focus on my investing business.I currently live a pretty cheap lifestyle, so I only need about $30,000 annually to live very comfortably.

It depends on your financial comfort level. 

If you're not looking to sell your current home prior to buying a new one, lenders will look at your current DTI on both home mortgages, not on the future DTI when you already have a lease/tenant renting your current home.If your income cannot justify having two mortgages that lenders are comfortable with, you may have to explore other ways to do this.

We'd be happy to discuss terms to make the lender comfortable.

He agreed to step up and handle the closing for me and I was completely comfortable with him doing it since he had more experience with real estate investing than I do.

But I have to warn you about the sadness inherent in the road you are about to embark on, and give you one piece of advice.A lot of people have very strong opinions about this topic and no one is comfortable consider that their whole financial belief system might be in grave error.If you go from being less than financially successful to most of your friends (as something like an English language teacher) to more financially successful than most of your friends (as something like a real estate investor), you're going to realize that for some of these "friends," a very big reason they felt comfortable around you was because you initially validated their mistaken financial worldview.

We were under contract escrow paid but we exited the contract due to a lead pipe and levels that we were not comfortable with.

Am I comfortable managing a property?