Use tax benefits like depreciation, repair deductions, and tax-free refinance proceeds to offset income, and consider an LLC for liability protection.

Some thoughts to consider:If you sell now, you are unlikely to pay capital gains taxes as your first 250k (500k if married and filling jointly) aren't reported.Doing your first rental remotely is undesirable without 1.)

The property tax is higher than other markets, but generally, the numbers still work. 

You can always use a software like Turbo-Tax and follow the prompts.

If you can rent it for enough to cover the principal, interest, taxes and insurance and still put money in your pocket, plus cash flow on the property you're purchasing, that would be ideal.

I understand that I need to account for taxes, insurance, and other costs—Should I go with a LML and then do a refi later on?  

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

I recommend that you contact a lawyer to setup this process for you.  

For tax purposes, rental income is generally recognized in the year you receive it, not when it is paid.

Salaries, compensation, rent, taxes, utilities, fees, MLS, etc.The flat fee model is a recipe for disaster."