There's deals that pop up here & there but for the most part I think it is over priced around here.You mentioned the seller has had it on & off the market several times so that must be for a reason.

I don’t know how well Cozy will scale but so far I enjoy its ease of use for myself and my tenants.. not to mention it’s free to use.

What they don't mention is that as @Ian Smith pointed out, the City requires a 20-point inspection vs. the typical 8-point inspection elsewhere.I'm a home inspector in Baltimore City and the consensus price I've heard bounced around is $200-$225 for the City due to the stringent requirements.

Not to mention that if the roof needs to be replaced on a SFR you will be the one responsible for $10K-$20K.

What are you seeing in those areas you've mentioned that looks like a fit for that price range?

It makes sense to focus on areas with strong fundamentals and, in particular, population and economic growth rates.You mentioned a few cities I hadnt explored before, so will be sure to check them out too! 

You lost me when you mentioned the “substitution for collateral”.

Like @David Gran mentioned, you can get two homes with the VA loan; I did exactly that (still have two houses with the VA loan).   

Here are some recommended resources (not paid for mentioning anything in this post:)Personal FinanceI strongly suggest learning as much as possible about personal finance (if you haven’t already) as I believe strong personal finances is the foundation for a strong real estate portfolio.

The issue he has mentioned with his properties is vacancy including one that has been vacant for 2 years because he was doing the rehab himself and him having poor tenants.