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

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. 

Power tools and heavy equipment?