Things, like how much money to invest, how long you'd like to invest it, do you need it to be relatively liquid, is it self directed, how much you make a year, your age, are you W2 or self-employed or retired, what other assets you have, there are tax considerations, and so on.Ask a local friend or a local tax preparer if they know of any qualified and honest financial advisors.

I can either put it in my employee retirement account which is not maxed out yet - (btw do I have to personally make sure I don't over fund this each year or is there some kind of monitoring going on?)

Is it paying for the kids college or having a nicer retirement?

I was a JTAC, retired in 2008.Your financial background may be best suited for lending, but Property Management is another option where you can learn to manage investments, what makes a good investment, etc.

My goal is to retire from teaching in 5 years.

We're planning to retire there (PEI) in a few years, and I'm in the process of purchasing a duplex in Moncton.  

I could actually live on that since my retirement home is paid for already.. :)    

This is referred to as the church house.5th up was a bank short sale on 61st street6th was a house occupied by a retired person that needed to rent it back for a month.  

Most of use want to retire sooner.

Many of the original owners are moving into retirement homes and many of the homes get sold the first time in 40 or 50 years.