Even though the cash flow is better than real estate, the risk of running it is more than what I can bear, and I sold it after 6 years.My dad was retired at the time, and I considered buying a small Chinese restaurant, takeout, and have him run it as manager, and part time if he wants to.

Can you explain why a seller shouldn't list/sell for what the market will bear?

If you are moving load-bearing walls and adding beams you might need an architect and engineer, while if it is as simple as some updated finishes and casework you could get away with less sophisticated designers.

That has a bearing on where you should probably invest.

I like the idea of not having to spend too much on the first deal or two to get my bearings. 

Zillow won't show you that the only thing separating a house from cashflow is an easy-to-remove, non-load-bearing wall...and Zillow also won't show you that the wall you want to remove is load-bearing, or that the noise from the street is way too loud for tenants--this stuff requires boots on the ground. 

If you’ve managed to untangle yourself from “paralysis of analysis” for long enough to explore your local market, here are a seven ideas to bear in mind:1.Keep it within 30 minutes of where you live: The reason for this is simple – for as often as you need to visit your investment house, you don’t want to drive away your day in time and gas dollars to get there!

From your post, it sounds like you plan to have access to more money than is required for the flips and that's the part that is confusing me, but bear in mind I've never used hard money lenders.Do you plan to present all 3 deals to the lender at the same time?

There is no record of a C of O with DCRA because, I'm sure, the property was built and previous owners moved in well before they kept C of O records.DCRA - a bear under the best of circumstances - is very unclear as to the proper path forward for us.

@JackWiley is correct that best practice is to escrow your security deposits in a interest bearing account.