If I buy a new property as a primary residence and move into that new house, will I still have to pay a down payment for an investment property if I plan to rent out the house I currently have after I move into the new house?

Also NEVER pay a GC upfront, ever. 

If you’re talking about paying over asking or having a larger downpayment: Those aren’t  expenses.

If they will take interest only for the life of the loan, that would be preferable to amortizing as you can likely do better than 5% interest with the principal money you wouldn't be paying.

So I wouldn't trust a bid from a Contractor unless you pay them, the other guys will just mail it in.

They have 529s to use to pay their living expenses and school tuition. 

Devin,Just a warning about checkbook IRAs: Self Dealing Activities will get your entire IRA disallowed and you will have to pay the tax on all your money.Self Dealing Activities are frighteningly easy to do.Do a Copilot search for "Problems with checkbook IRA plans."

What is the best legal structure to assume his existing land contract while either concurrently paying him or writing up a 2nd land contract to the seller past the 4 years on the current land contract?

I'm guessing the management company would collect all rents, pay expenses etc and the individual LLC would just own the real estate.

But I have used the MyFico site to improve my credit by myself, largely by paying attention to the utilization thresholds.