While this is municipality dependent, if the contractor is not licensed you likely cannot obtain the necessary permits and approvals.

If you're only using a portion of the funds, its less of a risk and could make sense depending on your situation and the deal itself.  

That will be an important piece to this depending on how you plan to source your capital.

Therefore, your long-term income depends on the city's ability to attract new companies.

 @Sri Reddy it all depends on your goals.

This would depend on whether your property is overvalued by the tax assessor and in turn you are paying additional taxes on that additional valuation.

Therefore, you would need to file partnership returns for each LLC.Given these considerations, both approaches could be correct, depending on the specific circumstances of your LLCs and state laws.

I think it will also depends on state laws and a lot of information not present but the HOA rules and insurances are two different things.

Expect rates to be higher than "typical" financing programs - right now, I'd plan for at least 8%+ depending on the whole scenario. 

Providing relocation assistance to tenants, for example, if I want to sell the property or move back in - this can range from one month's rent to thousands of dollars (e.g tenant has a disability, minor children, elderly it will cost you more), depending on the city.