I have helped many people find good income producing properties and may be able to answer some questions posted.        

So as an attempt to intentionally enter the world of investing I’m looking to purchase another property that will produce great cash flow.

The new 200,000 loan would still produce a cash flowing rental.  

If you produce a clean property with upgraded, separate mechanicals, I find that you tend to get a more responsible applicant.  

Here in SF everything has gone up a lot since 2012, so you really have to be innovative to get deals to work as buy/holds. 

sellers who want to receive benefits of selling a property that is not currently producing benefits to them.Too many people overthink think. 

Use a direct-response marketing campaign (3-step) offering a free home seller's guide.Use the USPS's Every Door Direct Mail (EDDM) and farm areas offering said guide.Ask for referrals.Do more advertising.Talk with top producing agents and see if they'll refer you to listings they don't want to take on.

You are correct; pulling probate leads single handedly is really time consuming and does not produce enough lead generation. 

I understand the need to use licensed/insured tradesmen for electrical, HVAC, plumbing,roofing and I will easily be able to obtain W-9, copy of insurance.However, my plan for flooring/sheetrock/painting/siding is to use sub contractors that may not be able to produce a legitimate W-9, may not have insurance, etc.Is this a bad decision?

Outside of that we tend to use BK flags as further insight and do a little custom configuring to produce our bids based on simple ideas of if BK is filed and if Proof of Claim is filed, then payment streams and discharge and dismissal.