Sometimes the tenant wants to renew the lease for their stability and I’m fine with that.

Aloha,What does your management agreement say about termination of the contract, and automatic renewal?

It's useful to recall that a MTM lease is exactly the same an annual lease except that the duration is shorter and tends to renew to the same duration upon expiration.For this reason you tend to have all the same options at the end of a MTM lease as you do at the end of an annual lease, with the same notice requirements, too.

Business was really picking up for him and we were getting close to $8-10k month and some months $14-15k. 1 year in, our lease was over and he wanted to renew it for a fixed rent price.

Lifesaver in winter especially.Because it's more fair for the tenants (they are billed for their exact usage), they are more likely to renew their lease and/or just behave better.

Today is Nov 10th, and he still did not send me the payment and has not responded.In July, when it was time to renew the lease, he also messed up on the renewal dates on the contract and was reluctant to get it amended with the tenant.

Aloha,First, check the laws for your jurisdiction...not all allow charging tenants for water.Submetering a multi unit will require either extensive re-plumbing or individual flow meters at each fixture, which will likely be costly.You would need to wait until renewal of each tenants agreement to make such a significant change in terms, and likely with 30 day or more advance notice.

I just send a check for their interest along with their lease renewal every year.  

Ultimately, I did not renew my VRBO annual subscription and dropped the listing.I think if your unit is suited to larger groups, you will do well on VRBO.

After one year, the tenant has renewed the lease along with a market rate rent increase.