After you start helping them, if it's a good fit they'll be more inclined to open up and share with you.

Or, if you've got the time and inclination (and you can access the city/county/state records), you can pull up each individual address and see when it last sold and for how much.Since you have Redfin coverage there, you could also search each address on that street, and scroll down the page to the Property History.Having an agent run 'em though sounds way faster and easier (and you'll get subsidy information too).Good luck!

Obviously I could just assign my PA with the seller, but then I'd have to disclose the assignment fee, which I'm not inclined to do in this case for obvious reasons.Can somebody here offer some advice on what'd they'd do / have done in a situation like this?  

if you feel you are more inclined and confident in sweat equities, go to REIA MEET UPS and offer barter for your sweat equity skills...Or if your inclined to keep a solo low profile..Find some cheap vacant residential acreage that may be dividable and call a survey company and divide it and sell it for a mark up or owner financed with enough down to cover your costs and maybe keep a chunk for your self...

So far I'm more inclined to work with investors instead of dealing with retail buyers.

I received a Masters Degree in Clinical Psychology over the summer.  

My inclination is to pay myself the last month's rent out of the security deposit.stephen----------------

If you have ANY inclination that this may turn out to be the case, then I would always suggest a fixed rate loan that is fully amortizing vs a variable rate loan that is interest only for any hold period longer than 48 months.

However,  his asking price is $445K, and after some market analysis and reverse cap rate analysis,  I'm inclined to think it's worth around $390K/$400K. 

We're I in your shoes, my inclination would be to ask them for an offer with an Earnest Money Deposit due within 48 hours of acceptance of their offer in the amount of $5000.