Just say no.I would almost never do this trade unless all my downside, including potential unknowns, were completely compensated for. 

Are you leaning toward a quick sale so you can focus on Oregon, or do you see potential in holding onto this Florida home as a cash flow play?

Rural tourism also seems to have potential, but doesn't have LTR back ups if you decide that STR is not feasible for any reason. 

Your property definitely has the potential to benefit from a cost segregation study.

That is over-the-top for my business, but I don't think it hurts to have an anonymous PO box in case you stumble upon a crazy person.  

We’re simply cheerleaders, fellow players, and coaches trying to get the new players to live up to their potential. 

If this job popped up out of the blue, your intent was not to move within the 1st year, so you may be ok.If you are planning on building a portfolio of homes, it is safest to stick in your home for 12 months to reduce the appearance of potential fraud. 

He believes that area where he will be buying the new homes is going to appreciate and attract more MTRenters, but now, the big difference is that he would now have 3 properties that can go up (or potentially down) in value, go up (or down) in rent, and three times as many vacancies to fill.My back of the napkin assessment is that for only a drop in $200 a month in cash flow, he would control a lot more assets with growth potential and as rents rise over the coming years, the combined rents will increase to a total more than the single rent.HOWEVER.

Additionally, don’t overlook Memphis, which has great potential for rental investments as well.

It sounds like you're dealing with a potentially suspicious situation.