Without accounting for management fees (I have not yet decided if I will try to self manage), and with planning to raise rents to typical market of $825 for each of the smaller units, and $1200 for the larger unit, does this seem like a worthy first investment? 

We typically alter our strategy seasonally, as demand shifts with the seasons.

You typically need up to two years of stable employment before a bank will loan to you.

Up front fees (outside of appraisal fees) are typically a red flag when dealing with a HML.

If it crashes hard enough, it impacts your personal finances, your relationships, and even your mental/physical health.With the exceptions of politicians and so-called charities, building wealth typically requires sacrifice and time.

I would also suggest letting them know what the requirements are prior to the showing, and possibly even allowing them to sort of fill out a questionnaire and making it known that failing to meet one or more of the requirements could result in denial of a tour however, everyone is encouraged to apply.Quote from @Emily Mohr: Thank you @Charles J Sabo, @Caria Mitchell, and @Matthew Becker! 

Also, consider this copy & paste advice below:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

His bank was in a state like Indiana, while one of his companies is in Wyoming, and just all sorts of weird sketchy stuff that accumulated over the period working with him.

I would anticipate a semi-guaranteed government run insurance program, similar to the national flood insurance program of some sort and perhaps connected to an existing department of housing program to manifest.

(The typical commercial loans I use are at 9.5% right now so be prepared for that.)4.