I have a chunky down pay and good credit but scattered self-employed income since I'm a student.

It seems like you are scattered on what you want to do, I find that If you can find your WHY, finding what to do next comes easier.

If it was a 23 door apartment complex, I would say that is doable for a first time investor.The fact that it's 23 single family homes scattered all around your town.... that's a lot.How do you know she even wants to sell all 23 doors?

It seems to me from tons of reading that the tenant screening process is scattered.

I know others will say there are some decent areas scattered around the East side, but as an out of state investor, don't test your luck unless you really dig into researching specific neighborhoods and streets.

I have about $10k to put towards a down-payment and an increasing variety of loan program options from some first time homebuyer grants (duplex eligible) as well as a mission-driven hard money lending program that's focused on getting locals to undertake scattered-site rehab and to curb gentrification from outside investment and yuppie tenants; then there's FHA 203k which I've heard can be alot to manage for a first-timer.

Most legal multifamilies will be in DC proper, and typically in Columbia Heights, Capitol Hill, Trinidad, Deanwood, Anacostia, with a few other scattered through the other neighborhoods.Properties that have, or could have an ADU, Accessory Dwelling Unit can be an option as well.And the most popular strategy for house hacking in the area is the rent by the room strategy.

We run a management company with 1200 scattered site units with about half being A/B class and half C/D class. 

You've received some pretty scattered advice here, and while some of the advice may work, there's no way to know until more details about the situation are known.Always happy to help and serve.

Otherwise you will have collateral scattered all over you can’t use.