We have a large house with a lake view that is currently rented to a retired couple while they build a house (cough, McMansion) on their own property just below the rental, directly on the waterfront. 

Ideally I am looking for something that he can stay in while he's there and do any work that needs to be done and keep it as a rental when he goes on to the next job.

I am looking for people to either share there knowledge with me or point me in a direction were i can achieve this knowledge.

Ideally you will get them on a lease of yours but it's not the end of the world if you don't.

Counterproductive to your end game.Roll the IRA into a self directed version and buy the property with IRA funds (you can get a non recourse loan too).As @Christopher Phillips mentioned, every property needs to cash flow with at least 70% financing or it is not a good deal from a cash flow perspective.Also, this $700 or so cash flow you are quoting, does that take into account all the expenses?

They said we didn't even come close, but a week later,a duplex directly next door sold $68K So PATIENCE,PERSISTENCE ,and PERSEVERANCE ........And away we go.I listened to a podcast the other day,he said  " PERSISTENCE + OPPORTUNITY= LUCK "SO I THINK THE A ANSWER IS TO TAKE ACTION WHAT SAY YOU ?

I feel like I'm going in 5 directions at once.

I have bought directly from the bank before, but not through this website.

You just took a giant leap in the right direction; signing up on Bigger Pockets!

I think @Adam Menconi is up in Santa Rosa, but believe he deals with some high-end stuff in the area, and may be able to help you out or point you in the right direction.