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

I closed a business over an executive order Jerry Brown signed when he took office that forced me to pay myself a certain rate on public works projects and do certified payroll on myself.

Which insurance carrier , what kind of product, what kind of premium/pricing for what kind of sq ft additions/building, what was your total payroll amount, etc. ?

For example a filing that is about to be send or a payroll tax return that has been filed.I think its BS to be dealing with that however, If I was the PM and had the client for a month I'd be pissed to have to pay someone to issue the 1099 as well for them.

quick books pro is expensive but once you buy it's good for several years as long as you don't have payroll, then you have to upgrade every 2 years.  

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.. 

As a wholesaler, it's highly unlikely that your seller is going to be a sophisticated operator. 

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

Does the approach change, if you live near the property or if the property is further away (in state of out of state) There is no difference until you get to a size whereby you can afford pay roll.

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.