As with the E-Myth I would like to devise a business plan with policy and procedure in which to not only show my lender and CPA team members, but also allow friend and family to understand the seriousness of this venture. 

Are there specific rules regulating whether lease options can happen in Jacksonville? 

(You don't know what you don't know, as the saying goes.)The entire purpose of laws, licensing and regulation is to provide frame work to protect consumers.

He did say that even with purchasing the new investment with cash, there are regulations that require a 6 month period before being able to cash refi the rental.

There are some legal documents and procedures you have to go thru regarding taxes and entity’s but yes it can certainly be done.

Be careful about posts like this.Legally, the SEC regulates fundraising in the USA.

While retaining a wall might help with zoning or other regulations, it could be a lot more expensive.

Both of these are SEC registered securities.However, if you weren't raising money and had other partners you wouldn't have to jump through the SEC regulations and could structure a deal differently which in turn would allow you to invest in larger deals without having to be an accredited investor.

Prior to vacation renting please check out your local regulations and restrictions on vacation rentals as some areas dont allow short term rentals.   

The kind of trouble where your talking serious penalties for violating securities regulations.