I’ve got excellent payment history and a great score.

While people have made a lot of money on housing appreciation, and for many, this has been their entire adult investing lives that this has been a potentially lucrative strategy, this is an extreme fluke in terms of the overall sweep of housing market history, and it's not one that I want to ride out, waiting for the next crash.I am a boring person who likes multifamily. 

I want to make sure I provide my tenant with required documents that can hold up in court. 

Your CPA can do this very easily and provide you documentation for your record. 

I have $30,000 saved but I'm worried I won't be able to get a loan since I wouldn't have 2 years of W2 work history since I am now commission-based.

Realtor also has a Tab for Tax History which shows the last year’s taxes.

Since your husband is still looking for a job and your teacher salary isn't huge (teachers are so under paid in Florida), you may have to stay with your in-laws a while or rent until he has some employment history. 

I do not believe you can buy in an LLC and get secondary mortgage funding unless your llc has at least 2 years of tax history.

., you have no history of successfully running a rental - that's going to be a pretty difficult task.

Know the history of the property and determine what advantages you may have.