I love SFHs, and that's what I deal in, but unless you are going to outsource most of the work with property management, 50 SFHs is easily a full-time job, even with the easiest tenants in the world. 

So, ideally we would sell the house to a retail buyer with some kind of agreement that only certain amount of land will belong to the house and we will be working to subdivide the land.Has anybody done something like this?

You'll hopefully never need the piece of paper, but just knowing (and remembering) what you agreed to is usually enough to keep things going on the right direction.

I'm thinking of items that aren't directly related to YOUR condo (like a roof) - but more like a swimming pool, or parking areas, etc.

.- I have to work under a broker for 2 years before I can apply for my brokers license in state of FL- I have to split my commission profit with broker and all funds/payments must be made out directly to the broker- the percentage commission I negotiate with property owners is my decisionDetermine best path to form Vacation Rental Property Management company being aware of my new status a sales associate- can I start my own business entity to establish and brand my VR management company now, or would/should I just wait the 2 years, get brokers license and then do so.

In the first deal, is it recommended to take a route through a realtor, or a wholesaler, or personal direct marketing?

You can send me a direct message with questions as I have years of experience in Sacramento county. 

Hello BP familyNeed your advice...So 2 weeks ago I took the plunge and started my first direct mail campaign in Phoenix.

.- Buy a direct marketing mailing list from kent Clothiers find motivated sellers list and mail to owners who don't yet realize they are sellers.- Call all the craigslist.org for sale by owners.  

While rent roll is important, do not expect to make it rich quickly- you must be caught in the direct path of rent increases (such as williamsburg, carrol gardens, park slope) and you had to have purchased in that area YEARS before there was ever a hint of an increase.