That said, I am looking for additional feedback for the pro’s, con’s, strategies, etc. to maximize the power of utilizing a HELOC funding strategy.

Chicago has several outer-lying suburbs to consider buy & hold strategies while your neighboring states in the midwest, like Indianapolis, have great economies to support all kinds of real estate investing.Out-of-state investing requires a lot of research to start and, as mentioned above, a lot of networking to vet the team you'll need to work with to move your project forward.Start by getting connected to a realtor who will have access to run comps for you so you can correctly evaluate potential ARV so you know what you'll need to put into your BRRRR property to maximize your ROI.

. - Buy in the best neighborhood you can - this helps to ensure an easy resale should you need to exit quickly.House hacking on an FHA loan can yield amazing cash-on-cash returns and set you up for financial freedom if you start out right.

Some say to focus on long term appreciation and don't worry about cash flow as much (such as the brrrr strategy) Others say to maximize cash flow right now.

I would recommend working a tax professional well versed in REI to make sure you're maximizing these. 

Sounds like you have a good head about the numbers you'll need to look for in the right property - you'll often hear "analysis paralysis" thrown around a lot with new investors... so long as you're doing your research ahead of time and you have your connections/network laid out (i.e. realtor/contractor/lending) then there isn't any reason you shouldn't pull the trigger when the numbers work.The important part will come when you turn over your investment to your boots-on-the-ground team who will be responsible for making your project move forward - making sure you're using licensed, insured, and fully vetted contractors will ensure that your money is being appropriately to protect your investment and to reach that projected ARV - the effort should be focused on maximizing your ROI so you can keep your momentum going!

Was in Aerospace for 15 years making rockets and satellites and a big life event happened in 2018, so I decided to pivot and try something to maximize my time doing things that I like to do and figured I'd give RE a try. 

I need software/Companies for the following:Skip-Tracing that will lead to successful cold callsTracking and maximizing efficiency while DFDDesign a Professional RE websiteSet up Google Adwords ads for specific locationsAnd anything to help with Direct Mail (IDK if that is out there)So far, I only know of lead propeller for Google Adwords I believe. 

Some investors are super gungho about maximizing leverage and putting down as little as possible as long as the property cash flows.  

I suspect that buying a rental will yield better returns than paying off a 7% mortgage.