We live in Lakeland, TN 20 miles from the Blue Oval site and I recently had a new BO employee rent one of my homes with a potential to sell in the Spring/Summer of next year.

I think its because there are a lot of people pushing seller financing right now and private lending because most cannot make the numbers work on a property - so the gurus need something to be able to sell so its this is the flavor of the month. 

I would lean towards selling and repeating.

However, we also recognize the time value of money, so while it might pencil out to turn a profit, but we get an immediate payback versus a six to nine month holding time, it might make more sense to sell them both as bare land.  

I could complete the main road in phases, build 2-3 at a time (could do more really as we have 15 right now actively being built but realistically not sure how fast it’ll sell.

Both on one loan may save you a bit up front in costs, but it'll make it more complicated if you ever decide to keep one and sell one.

If you're expecting property owners to sell their home to you at a discount, you'll need to earn their trust - whether that be by demonstrating a successful track record with purchasing/selling similar deals OR by meeting them face to face and separating yourself from the dozens of local investors and realtors.Lastly, I'd recommend searching past posts related to this topic as well as checking out books related to your target investment strategies.All the best!

On the flip side the clients I fund in my land deals are doing very very well in the foothill subdivision 50 miles or so west of the springs.. but thats the land game buy low sell high.. cant wholesale that stuff it needs to go on MLS to marketed and turn around time is generally 90 to 180 days but nice margins for my clients ..

You sell your investments whenever it no longer makes business sense to hold them, not when you "need" it for tax reasons!

When you add rehab costs and effort, holding costs, and selling cost there is not much profit.