Hi Michael, welcome to MA, I feel like Denver and Boston are always trading people back and forth :) My best friend moved to Denver and from what I hear your Market is just a nuts as it is here and prices aren't all that off so I think you will still feel right at home. :)As mentioned you can pretty much take Wayland, Newton and Weston off your list for that price point (those are extremely expensive markets).

I'm hoping to swing through the area in the next couple of weeks again for a couple of days.

There are two publicly traded REITS I know about that do this Farmland Partners (FPI) and Gladstone Land (LAND).In addition I hear pitches all the time about buying coffee, cacao, and other agriculture products in South /Central America.So I'm curious how you would differentiate yourself from them.I was a bit disappointed to see you say 'high total risk rated returns'.

Does anyone have any advice, either from experience or general trade knowledge, on lenders they've worked with in the area, or if this is even a good idea? 

I am a electrician that would be willing to trade my services For equity In a propertyI have over 34yr I have flipped 10 homes for others getting started to move forward for my self

Personally, I wouldn't trade peace within the family for a few bucks.Good luck.

Our friends put a $277k offer in on an un-finished home within 20 miles of this one that would require at least $90k to finish it to their plans, hopefully they can swing this $350k property & accept the extra travel distance.

I’m a contractor by trade so I can handle all the Reno work top to bottom so that aspect doesn’t worry me and I’ll save money on the labor.

One thing to consider if you think you might move back then keeping might make sense or be prepared to trade CA house value today for one bedroom Socal condo later for that same value is very possible. 

Fair is trading like value for like value - this is a handout of sorts (don't get me wrong, I am all for helping family out - it is just important we call it what it is and not confuse this with investing).