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.

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.

I've also thought about reaching out to one of these major portfolio lenders and putting everything on more fixed long-term debt to increase my cash flow, but I like the idea of paying everything off in 15 years.