In may of this year I was going to increase the rent but I gave him a chose to pay $50 more per month or if he signed a two year contract I would keep the rent at $850/month.

The fact that housing has increased much more than rents historically indicates that rent appreciation will be greater than property appreciation for a while. 

Rent is at the market so not looking to increase for this term. 

I'm working as an Insights Strategist during the day, putting in a few hours of marketing consulting work on the side during the week, and studying up on real estate investing on the weekends (and whatever time I have left over during the week).Having worked in the finance industry for the last couple years, I became increasingly aware of different types of investing vehicles, but never really considered real estate investing until I moved to Miami this last July.

If the tenant has a lease that expired a year ago, (ie: nobody can produce a current lease), then you just need to draw up a new lease, provide a month's notice of the increase, and if she won't sign or move out after the 30 days, consult a real estate lawyer or file for eviction.

The two considerations I would advise is:Does Cozzy charge a fee to the tenant when making the payment? 

However this would cause your interest rate to increase.  

Also, can't I also just issue a 60 day notice to increase rent by $200 or so.

How does everyone handle rent increases with new home purchase, with existing tenants?

I think i need to increase the volume of letters im sending each week.Thank you for the feedback it very much appreciated.