I am not sure if I would get the HELOC and the refinance from the same organization though.

Its an organization that utilizes the old railroad right-aways to form paths for walking, biking, hiking, Etc.  

The LLC's and how that is organized is a detail of the plan.

. – just each state’s LLC search (I intend to use Northwest as a registered agent).My question is when setting up the LLC in Georgia, would the “Wyoming Holding Company” be the Principal office address, Organizers Name/Address and Authorizer Signature/Title in the Articles of Organization or would I set up the GA LLC as normal and place the ownership in the Operating Agreement only?

I need to organize rent collection next week.  

If you are just trying to get going and focused on Chicago make sure to check out @Mark Ainley 's Chicago investor focused podcast:  https://www.straightupchicagoi...The one thing I've always found about mentors is that they have come organically. 

Here are thee tools I use:IGMS for communication with guests and automation of communication (free for 1 property)PriceLabs for organizing min stays on what days and for far out bookings as well as dynamic pricing ($20/ mo)Remote lock for my automated keyless entry front door ($6/ mo).

One of my biggest worries is that I'll spend too much time and effort on bookkeeping and organization.

Gothca and you have the ability to really scope out what your bidding on so that if it does not redeem your happy to own it correct.when i went to tax lien Auctions in MS  it moved so fast there was no way to know what the heck you were bidding on.. of course you had the highly organized groups with 3 kids and their lap tops.. and the auctioneer would favor the known locals.. this was Hinds and Rankin counties.   

Going with a licensed agent is suggested, as well as going with someone who is a member of a property management based organization such as NARPM (National Association of Residential Property Managers) or is certified as a property manager within their state.