Background:My fiancee and I live in San Francisco.

I suggest that you review the definition of conflict of interest, as it is defined by your fiancees' employer.  

My fiancee and I are on a somewhat heated debate about what type of property to invest in and make it our first home for about 4-5 years.

I trade Futures and the idea is to Buy Low and Sell High or visa versa, on any time frame that you can understand.

I can't tell you how often my fiancee's little interruptions to my work time, drive me nuts.  

For the particular applicant that raised this question in my mind, her friend found the listing, I spoke with the friend, then I reached out to the prospective applicant, I coordinated a time to meet and show the property to her and her fiancée; then she lets me know she is working with a realtor.

I would be looking to structure my deals through my Canadian entities as a JV with my friends LLC down in Florida that way I can get my TN visa and live in the US for more than 6 months at a time.My price entry point I'd like to keep between 150-200 at first with an ~30k rehab budget, what cities would you recommend?

what type of visa ? 

I remember back in the 90's, a survey of several hundred "millionaires" found only 10 or 20% had a Gold or Platinum Visa/Mastercard/Amex (status card), but over 70% of them had a Sears credit card!

Palm Springs vis a vis Los Angeles or Pigeon Forge, Gatlinburg, Sieverville vis a vis Knoxville, Nashville, etc.