Later I started using small local banks (portfolio lenders) that could provide purchase + rehab financing all in one closing, which was cheaper and less risky (didn't have to stress about a refinance coming up quickly!).

Lots of stress through the lending process2.

Honestly, landlords need to reduce the problems they face, not increase them. 

I promise you it is worth the money for the stress relief of knowing someone else has insured your property is your property.

How do you prepare for this and what strategies do you use to help reduce risk and continue to earn in a bad market?

At that point, we determine a break even point by adding "fluff" to the expenses (making them higher than stated) and reducing the rent rates / increasing vacancy to see if the deal truly works. 

That is nobody's fault but their own.Some firms do say the seller has to pay it which the buyer just reduces the offer price and can roll it in depending on the LTV for the loan.Most of the time listing brokerages pay a co-op fee.

The fact that it is a 401k with a current employer greatly reduces the likelihood that your parent could transfer any of these funds to a self directed account now (while working for the company).

I'm trying to understand how to reduce the uncertainty in feasibility analysis of a property development, and I thought some of you here might be able to comment from your experience.

When my girlfriend moves in she might pay 280 and then I will be saving for my next duplexKeep in mind that this 4 step process I outlined takes time (anywhere from 1 to 10yrs depending on the person) so keep the big picture in mind but don't let it stress you out too much.