I’ve been doing this for years, anyways I replied back to him with basically” thank you for your feedback I greatly appreciate it “ and move on. 

Creative or basic.

I had some "expert" basically call me stupid for mentioning I would be doing this.

Basically they get to use it for free in exchange I'm not going to repair it for them.

Basically, bottom line: Am I able to purchase my first property now using hard money and then refinance, or would I have to wait until I have 2 years of taxes for both of my roles in order to accomplish all of this?

So you'll have your zone which gives the basic perspective of what can be done on a property, for example in this case 'Single Family Residential'.

I align with you, that I want some basic operational data when assessing offerings, particularly an offering like his, where the deals are identified and known.

Piedmont is basically all single family homes over 2M so in terms of investing, it would be for appreciation only.

Basically just use what you got and don't do an addition from my experience.

In addition, anything that is 30+ days (or 1 month) is also not considered STR and this is basically all of Florida.