@Jordan MoorheadAs a Minnesota (temporarily a Wisconsinite) I've subscribed to the cabin religion my whole life and my near-retirement parents are trying to understand how to afford their own to retire with (religion makes us do crazy things ;)As near as I've been able to good naturedly guess, the cabin love is what you get when you mix the seemingly universal desire to travel with the home-body reserved demeanor of Midwesterners.

.- Since the farmer sibling lives very close to the land and farms it himself, any portion he owns is considered an agricultural investment and property taxes are ~1/2 the normal cost of property taxes.My thoughts:Allocate a portion of the land to each sibling and dissolve the TrustEach sibling can 1031 the land into a desirable rental property near where they live (if they want to)At some point in the future (5-10 years?)

He has no desire to be a landlord and wants the current tenants to purchase the property from him, however, they’ve out grown it and want to move.

Where should someone who has no experience in real estate, a desire to learn, & a willingness to be a sponge begin in real estate?

The issues I’ve found is that in desireable markets you can’t cashflow after a refinance so I’ve stuck to buying the normal way.

Home affordability in your area should definitely be something to consider, however, also evaluate if there is enough supply compared to the demand—and if the area is desirable. 

This is one of the few places left in NC where you'll be able to find deals that give you the cash flow you probably desire.

Dropped out of law school after year 1, because I didn’t want to go into an intense amount of debt and law is not necessarily the way that I desire to make my impact on the world.

The client has included terms she desires, but please let us know if you feel any of these provisions would be problematic in [Illinois] or if we are missing any [Illinois] specific provisions that would be helpful." 

In return they would charge you a higher interest rate on your mortgage.Talk with your lender and broker about your desired outcome is and they should be able to help you form a plan.