Instead of using my $30k saved up to use as a down payment for my first 2-4 unit, I would keep that as my financial cushion while I make the switch to becoming a real estate agent.

If you need an agent recommendation for the area, I'd be happy to pass your info along to a couple of people that are active in that area and mostly work with investors. 

Maintenance/cap ex will exceed $500/month (again hands off, if you do the work yourself there is huge savings).

Present:- Listing images- Property info (beds, baths, sqft)- Listing info (days on market, price cuts, etc)- Estimated ARV- Comps used to see ARV

Likely already known info for you, but maybe not for all. 

yeah so like, let's do the most expensive option vs. the cheapest: it'd be an extra $3488 at closing, but you'd save $82/mo ($984-ish for the first year). that's a 28% COCR, which most REIs would drool over!

I currently have 40k in savings for the next house purchase.

You could pull out $200K to $300K and Make a few extra payments a year and have that mortgage paid off in 8-9 years.If you pay the mortgage as a Bi-weekly and add $1000 a month you will have it paid off in 9 years and it saves around $225K in interest.

Any and all info and data would be appreciated.

.: Buying "off market" vs Buying Using the MLS - You enter the Blue Numbers and Out Pops the Red & Green Numbers.Red numbers are Expenses and Green Numbers are Savings & Profit.