Should I increase the rent?

[Allen Lopez]

So I have had an amazing family as my tenant for the last two years. When I posted the house to rent it out, they were the first to want to get on and I was going to charge them $1700/ month but I gave them the option that if they signed for two years I would leave the rent at $1650/month. The last two years have been great. The father is extremely handy, so everything something breaks I just order the parts and he installs them. They have not demanded anything except the screen enclosure replaced (which needed). Long atory short these are the type of tenants we all dream of. Anyways, the two year contract ends in February of 2019. Current rent in that community is $2000/month. So I am loosing money. I would like to increase it if possible. I would also like to give them the option for a two year contract again. My questions: 1) should I renew with a two year contract at $1650 again? My mentality has always been, rent low enough where you don’t lose too much but have the tenants long term. 2) how do I approach offering a price increase? 3) I would like to ask $1800/month if 1 year contract or $1700-$1750 for a two year contact. Thoughts?