We don’t know any PMCs to recommend in the orange county area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

I have no idea what I'm doing as I've never used a CRM before, so I can't compare it to anything.

Check Airbnb and compare your potential STR to the listed rentals and get an idea of your location and price point. 

If all of your savings are put towards the down payment you would not be able to satisfy this.

I'd compare coverages and narrow down from there based on what you want and can get.  

I’ve had it happen where the Bank was satisfied with having a lesser amount of phase 2 testing done than the environmental company initially proposed.

I would NOT be able to satisfy the second home criteria to occupy it for a month atleast in a year. 

I started looking OOS to other recommended markets but realized prices in my market are still relatively low when compared to other areas, meaning in the $225,000-$325,000 range for 3-4 units but there’s not much inventory.

Whatever you ultimately decide upon, make sure both sides are satisfied and agree to it.

It's like musical chairs and this will keep driving prices until the market finds an equillibirium between supply and demand, which all free markets will do over time, but since supply and demand are not that flexible it has to be price that will reduce demand until we are balanced.Milwaukee is also seeing a little bit of an increase in imigration due to climate change: smoke, fires, drought, hurricanes, floods, fresh water - in combination with remote work and low cost of housing compared to most of the country.