You will want to make sure it meets your criteria but the hard work of procuring the asset has been done and if you have a good partner then most of what you are looking at will fit your model.  

I worked for a very large syndicator back in the middle 80's doing asset acquisition ( CA re broker)  I would buy land developments and multi family as the procuring broker and on the land developments I would also marshal them through entitlements.

property #1 is the better cash-flowing deal, the only downside is the high up front cost to get into it, which will take a while to recoup and limits my 1-2 year plan to procure another property 

Most tax professionals will bring in a portion of the tax code on this that is not specific to rental property but is more general with regard to depreciable business assets in general, which is this:The basis of the asset is the cost to procure, install and bring the asset into service.So it's the "bring the asset into service" portion which then causes all kinds of costs to be added to the basis such as utilities during rehab, mortgage or other loan interest, property taxes, legal fees, etc.  

The new zoning conditions will allow for a maximum of 200,000 square feet of commercial space, and a maximum of 320 townhomes, apartments or other residential units within the development.A higher and better useOlson has procured and developed more than 3,200 lots in the Charlotte region in recent years, with the majority of that involving residential projects.

Even if you have an LLC I would say there is a strong public policy argument to piercing the veil, as you personally knew of the trampoline, did not do anything to cure the situation and failed to procure proper coverage for the liability exposure.

I am entirely new at investing but my family has been involved in this industry for quite some time. Now that I am in a position to infiltrate this industry I am ready to jump in both feet first. How big of a property...

It enables you to build relationships with other REALTORS and find deals before they hit the market. 

You've got to be kidding me.No buyer to procure. 

Speaking of license - isnt that on the operator to procure?