This brings me to this question: What kind of questions should I ask them to gauge how competent they are?

I am of the, "don't hate the player hate the game" philosophy.  

These are also the investors that will be competing with the new investor trying to break in the market when these overdrawn investors fall.I don't think it will be like what happened after 2008 but there may be some properties coming available here and there. 

I started churning a little bit... my numbers are way off, other investors are already on these deals, clearly I can't compete, yada yada yada.

It was a mutual win win but now new player, new game.

If you invest in Milwaukee you have to compete with all the local investors!

@AJ H.Sorry.No way for me to answer without knowing the property - its physical condition, current financials, the business plan, the market, the tenant demographics, and what you would have to pay for a competent maintenance person who has all the skills you need.And even if I knew all of the above, I would still have to analyze all the numbers and make a decision.I think at the end of the day, you will just need to make your best decision, implement whatever plan you choose, and wait to see the results.

There are countless other aspects to short term rentals (designing communications to please the booking platform algorithms, copywriting, the psychology of guest satisfaction, seo, knowing and understanding the platform policies to protect your payouts, etc) but it’s very intensive to truly optimize a property and that’s where a competent management company (with in-house specialists) would come in.

This is an industry I don't know, with players that I don't know, and with needs I don't fully understand. 

Definitely talk to a few and get competing quotes, ask about the size of their crew, figure out how often you'll pay them.