Then on top of that, their application process is a total joke.  

So what I'm looking for from you, the greatest RE community, is some guidance on which strategy I should go with, and / or more details about HUD homes.I'd love to connect with people who have:Gone through the process of buying a HUD home (so I could get a step-by-step)An agent that specializes in HUD homes (I've heard too many stories of unqualified agents dropping the ball)Experience in the University Heights market (I've been looking on the west side mostly)Experience with FHA / 203(k) loans (to go over finer details)I would be extremely grateful if anyone could help at all.

Maybe serve the tenant 60 days notice to quit and tenant to vacate before need to start the ugly eviction process?

In recent months I've personally watched houses sell during the bidding process for close to ARV!!

Of course, we have proof it is coming from exterior source, we mitigate the problem (hole/crack) and spray but anything ongoing is up to the tenant.  

What is your process?

I came across BiggerPockets as one of the first resources I encountered when I became interested in real estate investing, starting off with the BP podcast (I've marathoned ~60 episodes in two weeks) and the site itself.I'm excited (and to be honest, a fair bit intimidated) to get started in real estate investing, and I thought I'd reach out to the community to get more involved and accelerate my learning process.  

Late January, we get it rented out again.Between the process of eviction and the slowdown due to the holidays, it seems entirely possible that we'd miss out on 3-4 months rent by going with scenario 2, not to mention the expense and hassle of the eviction itself. 

Be realistic about things like maintenance, so many poor quality tenants that ongoing costs can be high.

We're in the process of suing the tenant for the back rent and damage to the unit and I'm guessing she called the city to report the violations to claim unsafe living conditions or something.