From your experiences, what is a good/effective/quick way to have the current occupants move out? 

Places like Maplewood, Richmond Heights, Affton, etc. would be where I would start (if looking at long term rentals).

Everything here is a trade off and if you're interested in long term planning, it's best to ensure you fully understand how it all works before jumping in.

As I get into short-term rentals, I’m curious: What should I look for when picking a location?

At this time, the types of properties that I'm interested in pursuing are primarily multi-unit rentals and short term AirBnB properties.

Real estate is a long-term wealth vehicle, and overall, I would be cautious about how you define overpriced.

Well, history shows what happened both in terms of marginal tenants ultimately getting hurt (as did many landlords) and the Supreme Court ruling the Eviction Moratorium as unconstitutional.I see the whole idea of rent control, which is just another form of government invasion for political hopes, being bad for everyone. 

If they just needed one more month, they might extend and pay the premium.I mention that, because if you are OK with the resident and just want them to sign a lease, tell them the MtM price will go up effective September 1, and is $400 more per month. 

Id suggest 2 or 3 yr term on both. 

@Levi Collins: As long as the tax deed clears title process, that should not be an issue.