This way I'm aware of the end buyers buy box before I go locking up contracts with sellers.  

I would make sure that you have an ironclad partnership agreement if you go into this deal with your former boss.

Its a great way to get yourself into the RE investing game.

We are starting out with flipping because, as @Mohamed Youssef stated, we would like to build up a bit more capital.

Since graduating in 2021, I moved to Washington, DC to pursue a civil engineering career and am now feeling like I am in more of a position to start learning and pursuing real estate investing seriously.

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $178,000

Cash invested: $10,000

primary home own use has an Airbnb/ short term rental 5 months out the year/sometim...

And welcome to BP.I think you are on the right path. 

My wife and I are interested in buying our next rental property, particularly a SFH and we plan to rent by the room, and possibly go through Padsplit and rent by the room.I own a duplex from before our marriage which is rented out on both sides and she owns a townhouse from before we got married that were currently living in.

Step 3: Compare build plans / specs to decide what you want to build.

competing against those in the industry is very hard .. .And your not going to have any luck trying to daisy chain these deals .