Of course site specific details could change my take above, but based on what you shared you need to buy a SFR in the two allowable areas above in order to obtain a STR permit. 

Based on your assessment of the spread, if it makes sense, then jump in and make an offer but try to push the settlement date back as far as possible to give you enough time to come up with a detailed execution plan for turning the property back into market. 

I chose to start with SFH just because I felt it won't be overwhelming and with it, any mistakes I make won't be that fatal.I am based in MA and looking to invest in MA and neighboring states as NH, RIOne other question I have is - what does it mean to get my finances tied up and ready to go?

Usually you get a long term loan from a conventional lender like a DSCR loan that is based on the property income.

I was also told that the LLC interest has to be divided based on the capital contribution and cannot be divided based on the work, for example it can't be a 50/50 partnership if one puts all the money and the other does all the work.Any additional insight or leads would be helpful!

The point to my comment is that when comparing equally a quality trainer and a quality forum IMHO the trainer will trump the forum.The knowledge base of the forum is so vast that without specific direction from a quality trainer an investor will be a little lost and may take the wrong direction to accomplish their personal goals.

3.c) Not be arrested at all (based on the color of title that my QCD will have provided to them), and will Trump have to evict them after proving to the court that my buyers don't actually have title to the White House?

Ben,The NOI on the condo if fair but based on equity versus mortgage $600 is a little risky knowing how Condo associations tend to hedge up on their HOA fee's.

I've been researching and see a few credit unions that do "ADU loans," where they'll assess property value after construction complete, then loan based on that amount.

based on this its what ever you all agree to and are happy with.. as long as you get some cash and you record your DT or mortgage in first position and then have co bene's on the mort/dt / note then thats all you really need.. you all might want to talk to a decent CpA about this.