Your realtor will be able to give you a much more detailed market specific answer but with house hacking and a VA loan it should be possible to get 0 out of pocket.

The sweet spot for us is sub 400k and we are looking mostly in NH, central MA and possibly RI for deals.  

They want to minimize their tax and/or refinance burden, to keep as much of the capital gains as possible to help fund their retirement.

I would prefer to sell the property vacant or the easiest less stressful way as possible, however I was advised that could deter investors buyers interest as the rental income is a one of my strong selling points.I am open and would appreciate any thoughts and/or suggestions from fellow agents or investors alike.Thanks in advance;)

You would have to quit claim deed your property from your LLC to your personal name and wait 6 to 12 months, If it was even possible.

Possibly one you have a relationship with. 

Instead of discussing the possibility of owner finance with sellers - what if I offered the opportunity to  JV where they are the equity partner?   

My piece of advice would be to try to take advantage of as much free education as possible with podcasts, forums like these, YouTube, and other real estate investors.

Also, how would I analyze the numbers for this deal, because there are various ways it could be used, either separate or possibly all together for a larger group.

Calgary is gorgeous, I try to get out there as much as possible when I'm free.