Running the numbers on paper is one thing, but actually securing bookings at your target rate is another.Sounds like you’ve got a good handle on your market and what your guests are looking for, which is key.

I was thinking of giving him 3 options.Option 1: He switches to a month to month lease changing to a weekly rent rather than monthly, the new lease will have different rules (ex. such as agreeing to a cleaning schedule and a liter schedule or trash needs to be picked up and placed in a trash can every 12 hours, human waste can not be stored in containers)Option 2: He moves out at the end of March, I keep the security deposit as rent and he does not have to pay February's rent and late fees.Option 3: I'll give him $400 to move out 3 days after we have this discussion.Thank you for any suggestions, I would like to handle this delicately as I don't want a squatter living with me.

You will be interviewed multiple times to ensure this is the right for you.

I've managed to secure the loan for the new house without having to sell the old house first.

You'd need to show the income on your tax returns and/or have a lease and first month's rent/security deposit for the unit you were living in.

Securing quotes for properties in flood zones can be challenging and time-consuming (especially if vacant), so it’s unlikely you could have done it quickly.

@Bruce Yi, depending on your state's laws, request a higher security deposit to reduce/offset the risk.

They find properties and approach Sellers and secure a price, then they seek out an end Buyer (you) and sell it to you at a higher price. 

It probably would have cost me about $10k more, but I would have still been able to secure the property.

However, before you do so you should ensure that your revenue from rental income covers ALL your property expenses in the townhome, including mortgage, taxes, insurance, maintenance/repairs, vacancy, property management, etc...