As already mentioned, you could sell via seller financing to lower AGI, as all you would have to claim is the payment income - until balloon payment received.Did know an investor that had 14 properties paid off and he moved into one every two years to then sell with the $250k single exemption.

On the lease, he'll pay me $100/m over my HELOC payment and all other expenses, including the refi cost, inspections, title work, etc... 

I did not do a separate criminal background check as I trusted the info from Zillow (Big lesson learned never to trust the Zillow data again in life).

I'd also like to try to purchase with a land trust or my LLC. 

Together, we have over $200K (mostly in stock market investments), and our parents may help with the down payment.

House hack another property with a low down payment loan and use the remainder or the proceeds to either renovate or purchase another investment property?  

Do they use a servicing company to make the payments directly to the , or do they make payments directly to the seller and hope they pass them on to the lender?

Best practice is to keep one or two payments in reserve from the buyers down payment for such instances.

I do not see why a down payment in real estate is "tricky".

All funds process through various channels but the PMS (with trust accounting which is very important) keep track of all the funds and then we disburse monthly to the owner.