Forget about the gross and look at the net..Seems like some kinda vacation rentalI know a lot of people investing in these type of properties and don't care much about the income but focus on how they can enjoy the property themselves with friends and family.. 

Direct feedback - re-prioritize what you are focusing on.

Home Base is the tricky one and our primary focus, we are interested in establishing a bona fide farm with value-added products.

I have no idea as to what your current ability, research level or grit potential  looks like, but when I made the leap you would have had to have put more than an army in front of me to stop me.  100% focus.

Although in this case it is a relative, let's not focus there because it will be a business relationship.

That means I want to focuse the next 5 to 8 years acquiring real estate. 

I love working on houses, meeting new people, and am currently involved in the medical field, with the goal of focusing in family medicine while doing real estate finance / investing simultaneously (can be a heavy load, but I'm learning to be tenacious).

The problem is that I currently enjoy my full-time career, which is not real estate related, and would rather focus most of my time and effort here.

Over the years, I’ve posted several tax questions on BP and there was an REI-focused CPA that was always very responsive and helpful in answering them.

Any appreciation would just be an added bonus but I think stability is my main focus.