Real Estate w/ Family?

So I'm currently in the process of full time IB recruiting, go to a top school/program. Dad is a business exec making 5mm~ annually and plans to work 5-8 more years. We own/operate few hundred acres of agricultural real estate as a hobby, that has appreciated substantially over the last decade we've owned it, but doesn’t generate much profit. We have discussed and are considering expanding into residential/apartment/hotel investments in the coming years. Siblings are establishing themselves in their own careers (and want to keep that going), I want to work a year or two for exposure, but parents have made it clear they don't want/need me to work in the corporate world for too long, but I want to help create something myself/my family can work on post corporate career. We have some decent contacts in the business (family included), who can help guide us in the initial stages, and a fairly decent network of contractors thanks to the farm business. The area we own the farms is underserved/rapidly growing, so feel strongly as if we've identified strong potential.

Was wondering thoughts on getting involved in a business like this? I like the idea of investing in undervalued properties where you can add value (fix up a mismanaged/inadequately maintained property), rent it to prove the property, and rolling the profits tax free in to the next larger top line property. We have the cash to invest & expand over time, but my dad is really busy with work so he'd be involved but I'd grow in to actually managing/handling projects. I think this would be my dream career, I could really see myself enjoying doing this day and night. Additionally, I feel like we might be headed in to a buyers market in the next couple of years in contrast to the current situation.

We do have some real estate exposure and fairly strong borrowing power given the farm land investments and income. We've bought/own a few single family rental units that have done well. Is this more of a headache than its worth? I feel the challenge/risk, and the mental freedom of actually owning the business would be really neat.