Could he extort the rest of the group or blow up the deal? 

They're also happy to commit to whatever your closing date is and blow right through it.

Attracting quality  might cost you more upfront but long term gains blow everything else away.

It's not fair to them to walk the interior and then after the first clean you say oh by the way I need you to blow of the porch, check and wipe down the grill, knock cobwebs off the front door area, etcetera. 

As far as allowing "outside" smokers, it's been my experience that they seem way too willing to just open a window in the dead of winter and blow smoke outside, even if it's against the rules.

Jersey blows for all of that.

I received a decent chunk of money, enough to start up so instead of blowing it off I want to make a good investment to generate passive income while I’m going into trade school.

This is where over improving or having underestimated the reno costs and overestimated the ARV will be a death blow.  

Execution matters quite a bit, but especially remotely, you want to make sure that the wind is blowing in your favor. 

I just had someone close on a nicer new-build townhome 15 minutes outside downtown Denver for about $200k less than it would have cost in the heart of the city, and they're blowing it out with design and amenities.