I have a fairly humble income, so not a lot of 'yearly cash' to put into things.He has the a healthy does of funds in his 401K at work, but is not planning on leaving that job for at least 3 years, and smaller amount in a ROTH IRA.

@Dominic Jones alright awesome we will exchange contact info soon enough.By the way if anyone in the DMV area and are familiar with Whole Foods Market in Columbia, (currently where i work) would like to come meet up and chat or eat some healthy foods with a slight discount on me...COME ON DOWN! 

I will lend all day to any rehabber who is:1. experienced - I need to see at least 5 HUD settlement statements, pictures of prior rehab work2. liquid - with adequate reserves (6 months of rehab loan interest payments in his bank account)3. good credit is preferred specially if you are not that experiencedBy the way, $250K/$300K is not 70% - that's 83% LTV.Lastly, I prefer one with "skin in the game" (10-20% downpayment - with me funding 80-90% of the project cost).If you don't have any experience, any money or any credit, approaching rehab lenders or hard money lenders is NOT an option.

This would allow you to buy pure rentals with 20% down .There are lots of way to "skin the cat".

Those things all create a very healthy economy, meaning a higher number of people can afford mortgages and rents. 

,Assuming that you're not personally managing your property (which I don't recommend unless you have the time, experience, and thick skin to do so), what benefit do you expect to gain for a property that's "closer"?

Some of the hard  money guys will require 10, 15, 20% "skin in the game" as long as you show you have the reserves.However, on buy and hold, which I suspect you're more interested in, I just don't think that exists with 10% down.

Looks like to me the owner wants you to have a lot of skin in the game, which makes sense.

Motivation1) Spend a lot of time with those I love2) Have options on how I spend my time3) Do 1 and 2 while my wife and I are still young and healthy

Skin in the game is VERY important :) That is for ANY state.