But for some reason I feel really uncomfortable getting out of my comfort zone going to a very sophisticated market such as Tampa Bay.  

However, my  experience also tells me that a school typically has a poor rating for a reason and changing the perception is no easy task. 

It's Perception! 

so much of this kind of work is establishing some sort of personal reparte'I will be curious to see how well US folks respond to you... just logistically our night is your day etc.and it will really depend on the sophistication of the sellers rep or relative.I know these styles of transactions we personally do here in our market need a bunch of hand holding and porch time... at least for the very good deals.. 

For your 1st deal, it is very important that it 'works' fine since this will build up your perception, confidence and overall experience towards REI (positive or negative) for the future deal. ......good luck and happy investing... 

Developers frequently assign development contracts and even large commercial investors have gained some notoriety in the past couple years for making large profits off of option contracts that were sold to third-parties.It's easy to say that a judge will tend rule against wholesalers just because of the nature and perception of their business; but to-date, nobody has been able to present to me any case law that supports this assertion. 

It does suggest a higher level of sophistication, so if you are trying to get wholesale deals it may be a little harder.

From the people selling you assets for a much larger discount than you would get in other markets to the difficulty of dealing with (or finding someone to deal with it) rehabbing or property management, the fact of the matter is the market is a lot less efficient than other markets and until that changes returns will probably be higher for the right strategies.3) Perception - For many reasons people have a negative view of landlording and many forms of RE in general.

As a result you can make the IRR say pretty much anything you like by changing some assumptions.Since your investor sounds like a financially sophisticated person, a way to impress him or her might be to run a "sensitivity table" that shows various IRRs depending on the inputs.

In psychology it's called learned helplessness and is not always the reality of the situation, just the perception of those who suffer from it.