I'd highly recommend local meetups and talking to real estate agents.There are companies that offer help with the execution of rentals and BRRRRs, but this typically comes with a large chunk of upfront fees or cut in equity.

Perhaps this was short sided, but the real benefit to us was that it cut our living costs by almost 50%. 

Most lenders require you to have 6 month seasoning to do a cash-out, but I do know of an option that cuts the seasoning period down to 3 months.

I'm thinking between your fanatical approach to savings and cutting expenses for two years and their gift money for two years, you should have a big chunk of money where you can go after this concept on your own.

It is important when to know how quickly to cut ties and when to give them a second chance, but this does take experience. 

Yes, we did.Here is why: market was a falling knife, loss next month will be worse, subject property not properly insured, and pants on fire "person supposed to pay borrower" is going to cut corners and try other tricks.

Note:  from a "buy" standpoint, unless you are all cash/heavy down payment, today's interest rates for investors in the 6%+ range don't cut it. 

Given the uncertain neighborhood prospects, I'm torn between enduring potential long-term losses or cutting them now.

Not everyone is cut out for sales.. there are skills in sales that folks just dont understand..

Here's another - the city literally hired a team of 7 people who do nothing but drive around looking for long grass to mow and then bill the homeowner (usually an investor) $270ish for a single grass cut.