HSAs and taxable funds are both fine ideas, but don't hesitate to add the Roth IRA component. 

I'm close (within a few months) to being able to completely leave my W2, but am confused as to how those practicing the BRRRR strategy without a W2 are landing long term financing for the refinancing component of the process.

I'd focus on a metric that is better suited to residential investing- cash flow, ARV, CoC, whatever aligns with your investment goals, but using a cap on a residential investment won't give you appropriate valuation on your return. 

CHICAGO... where you are from.Let's say you thought Appreciation was only the Gravy and that you will only qualify a property based on Cash Flow and NOT future appreciation.Imagine this was 10 years ago.You would be at the point where almost ALL of my friends and family in NYC are at this very moment.... completely priced out of ANY real estate in Brooklyn (and in your case decent neighborhoods in Chicago).In reality there are 4 different ways to Analyze Real Estate:1) Cash Flow2) Mortgage Balance Reduction (think about a 30 year mortgage disappearing at the end of the 30 years)3) Tax Savings and4) AppreciationIf you Master analyzing Real Estate for all of these components and treat them not as GRAVY but as actual components, then you would begin to build and expertise on how to do Analysis on NOT JUST CASH FLOW.You will develop your expertise on calculating Appreciation as well.If you ZERO out 4) Appreciation, BTW, you still have the other 3 components.If you ZERO out 4) Apprecation AND 1) CASH FLOW you still have 2) Mortgage Balance Reduction and 3) Tax Savings.Let's say you ZERO out 1) Cash Flow (because your Tenants will pay all of your expenses including your Mortgage payment but you get no cash flow), 3) tax Savings and 4) Apprecation.That leaves you with only 2) Mortgage Balance Reduction.Why did I isolate this?

You want to find someone you know well, has aligned goals, and can get along with. 

But because i wasn't clear I ended up causing both of us headache... .. another thing When they bring you a deal or respond to your request for quote for services, be quick to respond back and be ready to pull the trigger when all the stars align for you.

If you educate yourself on the space and the market and align yourself with people who are where you want to be you can start today.

Client should obtain full disclosure/ history information from the seller prior to close.Several problems can occur when the racking method is used :· If the racking method has been used, shingle joints align everyother course, which increases the chance for roof leakage.· Using the racking method requires leaving the last nail out ofevery other shingle to allow for the installation of the nextcourse.

The most successful people in this business have relationships they build & fall into the type(s) of investing that align best with who they are as people. 

HVAC System:The HVAC systems consists of 3 components – 2 furnaces (manufactured in 1994 & 1994), 2 AC evaporator coils (manufactured in 2015 & estimated in 2001) and 2 AC condenser fans (manufactured in 1995 & 2001).The 1st floor furnace is not operational and 2nd floor AC is not operational.