I recognize that (in the equity market anyway), it's quite difficult if not impossible to time the market and time in the market is more important than trying to time it.

You need the bank to recognize your increased value so you can unlock the equity...or you'll need to sell if the bank doesn't want to play ball.

You sound like a genuinely great person.

Now that I've recognized the mistakes I made, I can change up my approach and focus a little more in the better neighborhood.

That's like saying because 90 percent of investors fail REIA's should not exist.Hopefully some agents that come across this post will recognize the benefit of a group and connect with me, then we can help each other not become a statistic :)

Feel like the train has left the station here in Denver and I am not on it, so want to learn as much as I can as quickly as I can to be able to recognize a deal and act on it if I find one. 

I am just hoping that you all can help me possibly recognize some risk I am not noticing? 

Well, Tiny Homes are recognized as a mobile home/trailer right now.  

I recently discussed this with the Residential guy at my bank on how to structure this situation, the Feddie Fannie, FHA Rules are funny with this stuff, unless you structure it right, the GSE's will not recognize the amount applied to the purchase, in their eyes it will be a discounted purchase price, and the buyer/tenant will still need the down payment,  a smaller bank could hold an in house loan for 6 months an then re-fi them to a GSE but that will cost the buyer/tenant a ton extra.  

An LLC may not be the best route, especially if it is not recognized in New Zealand as a flow through entity with respect to taxation.