.), then the government will automatically charge you a 10% penalty.

Not an automatic disqualification, but definitely gets more scrutiny.

I would consider opening a vanguard mutual fund account and just leaking say $100 month there automatically forever.

Cash up front can be a sign of trouble, but is not automatically trouble.

Other direction, actually, I'd rather over-pay (& I do in fact overpay, relative to market) and know that I'm getting a stellar high level of service, communication, speed, smoothness, etc. 

An automated message popped up that said something along the lines of "the property will be listed with an REO" and the call automatically ended.

Attorneys in MA as automatically brokers so they're well versed in RE law and practice so I would check that they know how to specifically structure your deal. 

I am trying to get up to speed ASAP learning to PM my one and only property.

Nor the first scammy contact I received.All of the others have come from AirBnb, largely because of their push to have me lower my pricing, and take the first few with automatic booking.  

Those loans are hard to get because they're too small don't generate significant revenuethe properties get vandalized because all of the sudden they're the best house on the streetthey're a magnet for crime because that must be where the money isyour cash flow is eaten up in tenants that don't pay and fixing things that get brokenthey're just really risky in generalI say go a little bigger and get loans that lenders want to give, go with tenants that will have some pride in where they live (keeping your property clean and in good repair) and bring a sub par property up to speed with the rest of the neighborhood.