Check in with @Joseph Chiofalo they work multi family nationwide and would be an excellent initial feasibility resource.

My house worth $325,000 right now and my family is definitely moving to Dallas Texas in the next 3 years. 

What I have been seeing is that current estate planning is NOT serving modern society and families.

Quote from @Johnnie Fair: I wouldn't accept her application.When checking landlord references, many applicants will give you the number of a friend or family member that pretends to be the landlord.

My idea is to buy a house and rent it out, so it can pay for itself while I live in a family-owned house.Would you recommend buying a house in Orlando right now?

1st of all corporations own less than 2% of single family homes, they have actually reduced thier share of buying recently, now investors continue to buy up properties, it’s just more mom & pop types, all that said the housing market is in an extremely strange place, I could make strong arguments for prices pulling back, reaccelarting, or being basically flat, the biggest thing I’d advise is looking at you payment, comparing that to what would pay in rent, figuring out how long you plan to be the house and making an decision based on that, generally in that under 400k price point, breakeven for buying a property seems to about 3-5 years if you plan to stay in the house longer than that, bite the bullet & buy, if not rent.  

I'm about -$1300 a month on a Bay Area SFH, largely because I'm renting to family members so they're getting a great deal.

Neither of those properties are multi-family, though.

Spending less time working and more time with family, feels great. 

It's a single-family that you want to room hack or two-family that you want to house hack?