Playing an appreciation game can be risky.

And always have the ability to fire a builder and pay out for work (which is why you don't want them to front load the contract) in case they simply aren't producing.New construction seems risky. 

Yes, there are many different ways to get it back, so the risk is low.

This seems crazy as the risk is different, the rules of what you can do with the cabin is different, and most importantly the price difference between cabins on land they own versus forest leased land is extreme.

It seems like it's less risky because it's cheap. 

Do not pay them in full before they close all their permits.Flipping multi families is less risky.

From there, you will learn exactly what to do with your cash so your risk is totally minimized.

My realtor thinks we can still make it work and meeting the ridiculous appraisal requirements imposed by Chase is less risky to the deal than switching lenders. 

At least for biz class Yes, but it is also risky (e.g. you may not find a deal).  

Risk is fixed costs when transaction volume is low, you have to manage your cash flow.How many deals are your friends doing?