I can give you some advice that I learned from personal experience, and from also taking a BP course on multifamily.1) Are there any particular sub-markets within Orlando that are well-suited for small multi-family investment opportunities?

Smart buildings equipped with IoT devices can enhance operational efficiency and tenant experiences.

Mostly because we have family/realtor there who have experience investing in West Lafayette.

I love the flexibility to be able to do what I need to do for my business and my investing and have always had a great experience. 

Does anyone have any recommendations for a real estate agent that has experience with VA Loans (specifically- assumable VA loans)?

Underwriting will want to see some progressive experience in renovations, but as long as your not taking a quantum leap, it should be do-able.

But in my experience most sellers don't know about the AFR rules, and are willing to accept the Buyers terms as long as they ultimately get a price (value) on the property they want.

I would like to hear about your experience with them.They are affiliated with Cogo Capital.  

Your experience, cash position, risk tolerance, handy skills, and income levels all will play a role in what will be the best house-hack for you or not. 

I do have some experience with property management.