I have 12-doors there and a super strong team/operation.

There's so many catalysts for population and job growth (Intel, Honda, Amazon, Nationwide Hospital, etc).

In this case each job its associated with.If you can afford it and are scaling some what you can enlist a proper accounting team.

Make no mistake, being an operator is being a business owner.

2) How will Wyoming's laws and regulations affect the management and operation of the LLC? 

@John Dawson the best thing I can recommend is 1.) find a mentor you get a long with who is willing to show you the ropes and just be willing to grind like your life depends on it.  1-3 years of that will set you straight, so long as you're putting your clients first, and doing a good job.  

Is this rental income just added on as income during filing in addition to my income from my main job?

In some situations, it may make sense to hire a pro to get the job done quickly and correctly, then you can rent it out earlier and offset the additional cost, or at least part of it.My first house took me six months to renovate.

Your profile mentions that you ahve ownership in an LLC - WoodRich Hospitality Services LLC.If it is a multi-member LLC, there may be a separate partnership return required.If it is a services based business, there may be a benefit to operating it as an S-Corp to save on self-employment taxes.

I would like to expand into real estate to further that objective but my primary motivation is that I'm bored with my W2 job and need a bigger challenge.