In summary they have ranged a lot of the REI scenarios and I learned something at almost all of them even the building of 3 new units which is above my comfort zone (I learned it is ~$100K to break dirt on a new SFR which places a bottom value on any SFR).There has been no selling.

Some people are comfortable using a HELOC for buy and hold but I like the idea of flipping better because I am turning my money faster and can pay back the HELOC in just a few months so in my view the money is at risk for a short time.

A lot of times, good attorney/client relationships are based on comfort and trust.  

I would definitely consult with the town building inspector, because every states codes are different ( all based on the same code but some states add or remove, making it there own version) but i'm sure you could use a solid core wood door or a steel plate over a solid wood core ( installing this one in a commercial project in about a week). the closer would be required, but even if you are not required to have a peep hole, you may want to install them, not expensive and it gives your tenants a sense of comfort. 

I feel like most of these units are in dire need of basic updating which I feel comfortable with.

Doesn't have to be local CPA but if that's what you want, then certainly do what's comfortable for you.

Are you comfortable with accepting Section 8? 

That's a new one on me, I set the price for my market where I am comfortable with it and I know it will rent.

I am working to balance my position here because I have inherited the relaxed lease and informal rules from my father.

Regardless of what I got I felt more comfortable in the construction business.