I don’t live in your area but I would think in a house that size you would spend your entire $20,000 on the kitchen alone.

Chad,AFAIK there is nothing to preclude you from protecting your interest in the property as lien holder.

it is getting a bit tighter/tougher for new folks but if you spend some time learning the process you can make some great returns.  

Save the $ you would spend on housing for future down payment.Rinse and repeat until you have as many units as you want and you can buy a SFH for yourself. 

I live in the NE Ohio area about an hour south of Cleveland, but also spend a great deal of time in NW Ohio for college.

I'm setting up two LLCs with one for the flips and one for the rental properties.The flips will be an S-Corp exactly as you said to try and make room for some of that income to be taxed at a lower level.Having the separate LLCs is necessary not only for legal protection, but to keep the accounting separate.

If you plan to buy a property using a land trust for privacy protection, how do you go about making offers? 

To legally protect yourself you need to stay the course on the eviction.

If I do want to move forward, how should I structure a contract to provide me maximum contingency options and protections?

However the monthly payments are still considerably lower than what I can afford, and I am also largely financially independent at this point in life.I scrimped and saved til about age 37....now I spend pretty freely as even doing so I have much more coming in than going out.