My strategy is to play the long game and generate marginal cashflow while I hope/wait for continued appreciation (in equity and rental rates). 

That all money and credit needs to be generated on banks balance sheets, in other words, banks (real people who run them) have to be willing to lend those printed fed dollars into the real economy to increase the money supply to chase fewer goods and services, in the real economy, which i.m.o. has bifurcated from the financial economy. 

I may be wrong in assuming this but MOST agents have your best interest, it's how they generate more business by making sure you have a good experience.

They supposedly generate state-compliant rental agreements.

But I'll have to put around $27,000 down, to generate 300-400 a month, or about $4500/year.

If they are busy with Sales, which generate big commissions for them, they may not have the availability or focus that you desire, even if they have a big "team".

Time to get over the PTSD of a once in a generation market crash. 

This is extremely common here because there is almost never a Will involved, and typically, there are two or more generations of potential heirs to run down and deal with.

Also, the $250k price was chosen so that the property would generate cash flow for the wife based on $2k rent/mo. 

Legitimate self-employment activity or active business that generates "earned" income and absence of full time employees - that is how someone can qualify for a Solo 401k plan, you don't have to have an entity.