I would also suggest to make many offers when you are comfortable and ready.

There are a million options and it is which one fits you and are you most comfortable with.

You need to be comfortable with the offer you are putting together.As far as hiring a GC to do a bid to cover everything. 

I am able to lock in a rate of 3.75% with a couple pts, so my COC goes up to 10% and I am comfortable with that.  

My advise would be to focus on the sales side first and once you get comfortable and confident making money that way, then look to develop a management arm off of your sales business.

I also want to retire around age 50-55 comfortable, which I would define as 150k/year in a lower cost city, and the retirement plans aren't good until my 60s.That is my goal, nothing more or nothing less.About me:I'm a mid-30s single without kids working in the Pacific Northwest , making around 190k on a W2.To help you understand my mentality, When I moved here several years back, I did not buy a house which in the appreciation mindset was a mistake.  

I believe it's up to you and your partner and whatever you both are most comfortable with and agree to.

The primary reason I was looking to do the rent by the room approach is that as far as personal space goes it's not a huge concern of mine to sacrifice some comfort for a year while I have to live at the residence.

Then you could go in without an agent if you feel comfortable however, you will rarely overpay with a buyer's agent but you have to find good ones and commit to them or they will leave you on the dust as time is their most valuable asset.

As @Pat L. rightly said, you have to get comfortable with debt to scale in real estate.