Not to expand on the "family dynamics" but I would personally be concerned about having to deal with family requesting access to the property for periods of time as well.

People can expand or contract your thinking and thus your goals...

And i'd also like to start building my portfolio and expanding into small multi's. 

you can use retirement funds as reserves as long as you have the ability to borrow or withdraw against it. you'll have to provide the account guidelines from the holding company to show what access you have. for example my USAA IRA allows me to borrow like 50% max (think) so they will allow 50% to go towards my reserves. 

MLS should provide you more than enough properties for practice, especially if you expand geographically to understand a larger area, not a lot of people with off market stuff will take the time for kicks and giggles.

I like the search features: https://www.biggerpockets.com/searchAlerts can be really helpful too: http://www.biggerpockets.com/alertsThere are a few self-contained guides that you can access here: https://www.biggerpockets.com/guides

I’d have to figure out an easy way for the Airbnb guests to access my unit as I do not have a keypad.

Hey Lexi,Mind expanding on this?

My local library offers free access to Lynda.com courses so I think I'll do some training on QuickBooks.  

In Florida, my recommendation is that you expand your options to the suburbs of Tampa and Jacksonville/St.