It’s going to be an extra $270/mo, they didn’t blink.

You don't have to want to be an agent or to list your own flips to get your license.

Which he mention has that he has yet to smell it, but it could be an issue.

I don't think it will be an issue other than possibly financing. 

I am also sure that there would be an equal argument for a detached SFH with a property manager too.I think it all just depends on what you are looking for, and how active you want to be.

Again, your attorney (experienced in REI, not just a RE transaction attorney) is your best advisor.If all of your partners are both investors and GPs, then a JV should be sufficient.Money spent on professional advisors, whether attorneys, CPAs, etc. is well spent and will improve your returns and reduce potential headaches in the future.It also looks like you have a bridge loan on this property which, given this market, could be an issue at year 3. 

I’d suggest starting out by networking with as many other investors as possible and be an active participant in the forums.

The primary residence regulations won't be an issue for you while you live there, and when you move out then you could change over to long-term tenants.

Should I be an anesthesiologist or a surgeon?

It's NOT a perfect strategy for all, most or even many situations (I can't stress this point enough) although this sounds like it may be an ideal situation for such.