What sort of systems/automations did you have in place before deciding to quit your 9-5 to pursue your real estate investment business/career!

I would greatly appreciate if someone could provide some sort of input on the Staten Island market and

Building up a real estate empire is a fantastic idea in theory, but in practice unless you're incredibly lucky, you'll be better off putting it in some sort of truly passive investment, like Redfin stock.I believe MOST people here do not realize how problematic real estate investing can be, the degree to which luck plays, how little is truly within one's control, and how inefficient and illiquid the real estate market is. 

Also make sure that your CCRs or HOA allow you to have a long term rental back there and that the thing is not limited to family of some sort.

I am not looking to provide monetary donations to other community programs, but would be willing to invest significantly in some sort of community outreach program of our own. 

There are some instances where it makes sense to file MFS.The big disadvantage to MFS is that it disqualifies you from claiming some of the major tax credits and deductions available to those filing jointly.I would recommend you consult a professional to help you sort it out.Hope that helps.Ed

Keep in mind that HML will require you have some skin in the game and have money to rehab. 

Often times they have lots of experience with all sorts of repairs.

I have 0 experience doing this, i've only been listening to podcasts and browsing the forums for the last 6 months, so this would be my first real estate deal of any sort.  

On top of the units that I own, my family has over 100 rental units in Central MA and all are self-managed, but we also have a construction company and de-leading company under the umbrella, so it's been a vertically integrated sort of deal since I was young.