If it is, it would ideal in terms of flexibility.

I know there are some peak periods with festivals etc, but wondering what the rest of the year looks like in terms of occupancy rates. 

But in terms of money in his account each month, that $250k+/month of pure cash flow is hard to beat)

@Brian Gerlach,Yes there are similarities in terms that both are tax-deferred retirement plans, both can be self-directed allowing alternative investments.

I don't really understand your logic in terms of what you plan on doing once you've identified the area of cheap homes. 

Plan sounds somewhat vague in terms of "putting together deals/reports" to be honest, but it also sounds like you're trying to wholesale properties while being the agent.

But in terms of RE attorneys, call Jason Fowell . 

I think Lingo has his head in the right place in terms of protecting his assets.

I'm thinking in terms of a long long term hold, possible 20yrs +...Would love to hear from long term folks/pros on how to weather that or anticipate and "rebalance" your portfolio, for lack of a better term.

As a primary residence someone may pay what he wants, but if the numbers can’t work and he has reached the end of his rope in terms of negotiations then you may just need to let him know and say to keep you in mind if he has other opportunities in the future.Try not to get tunnel vision on one potential deal.. there are always other opportunities out there if this one doesn’t work out