Am I getting greedy to ask for an additional seller credit at closing to help offset some of repairs needed?

In most single family zoned areas adding a single ADU is not a value add meaning it will not add more value than the hands off cost of the addition.  

Udemy and Coursera have affordable options, and they could help you feel more confident when pitching yourself.It sounds like you’re in a great position to get started.

I'm not factoring this in right now, going based on the numbers I see.Definitely able to put down additional funds to be creative with a lender, at the numbers you are thinking. 

There is a processing fee if you choose the credit card option, but a direct ACH has no additional charges.

Both properties have a substantial amount of equity that’s essentially sitting idle.Would it be a good idea to tap into this equity (through a HELOC, cash-out refinance, etc.) to fund future fix-and-flip projects or purchase additional rental properties?

I have a large lump sum saved in an investment account for down-payment and any additional costs.

This creates a negative initial position.

I know in residential lending you can get a HELOC to borrow a down payment to buy another property. Does this exist in the commercial realm? Current value of paid off property is roughly 350k , looking to borrow 75k-1...

I was interested in something like owning a rental property as a way to generate some additional income.