These are just a few of the questions I am working over as I decide to invest locally or remotely.My personal answer is to start off locally, to gain some experience and an understanding of how the process works.

i am looking to gain more knowledge on the creative real estate business.

I am  looking  to gain financial freedom why helping others along the way. 

Furthermore, the property is cash flow break even, thus any gains will be in the appreciation, small rent increases in future years, and principal pay down.

One that is on the title, and another that acts as the contractor so "owner" can hire "contractor" to do the work.Tax reasons... capital gains reasons... etc.

The impacts of the LLC on the down payment, mortgage/capital gains write offs, and cost of business are significant, plus I can see making mistakes in setting up the LLC as so much of the process is new all at one time.

Do you know a broker that would let you hang your license with him just so you could gain MLS access?

So with my end goal being to own multiple rental properties generating cashflow here are my questions:Should I start rehab in the spring and try to list right at the 1 year mark to only pay short term capital gains or wait the full 2 years and pay no tax?

You will be losing all the equity you may or may not build.The FHA 203k loan program is a bit different and does not limit your gains.  

You can easily lose capital gain rates, plus there is the issue of refinancing.