But, they still require time and effort.

You should not get a PM until you have scaled to a level that requires it.

KNOWING real estate (or delivering babies) is a requirement for an expert. 

I told her that I’d hire her at her minimum required salary and give her a small signing bonus.

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

REI is full of surprises and they all require money.

Yes requires higher downpayment but can get down to 30%.  

Multi-family properties many times provide a better return per square foot than single family, which would be to your advantage as well.As long as you're mindful of the reinvestment requirements and purchase at least as much as you sold and use all of the proceeds, you shouldn't have any issues with this strategy.

I don't ever stiff the housekeeper and if this was a long term tenant who needed to break early I would do it but probably not in this case, again unless regs require or mom presents a more compelling case. 

It is also important to consider the transactional fees associated with originating the HELOC, whether an appraisal is required etc.