I’d expect my contractor to know the latter, so things like what size drain line to use but for things like set backs that would be better suited under the scope of an architect or similar role (and even they get it wrong some times too!).

For loans that size, you are likely working with a bank rather than agency or bridge debt. 

My fiance and I live in a mid-sized city, where the average single-family home will run around 300-400k and could rent upwards of 1500-2000, depending on size and neighborhood.

If your rents are $1,900 for a similar size unit, you may now have some competition.

I found that I get much better success with FB marketplace, although a lot more tire kickers and flakes as well.I would not compromise on tenant screening under any circumstances as it would be more expensive getting rid of a bad tenant.

For a multifamily only your % of personal use of the building will qualify for the 121 exclusion (2/5 year rule)So if you occupy 1 unit of a 4 plex (assuming all 4 units same size) 25% of gain can be excludedYou can however combine this with a 1031 exchange and defer the gain on the other 3 units into a new rental property 

Such services should include: - Creating enticing market listings and ads promoting the property at its best for high demand - Rental market expertise to provide recommended rent amounts for your property's market without recommending an inflated rent amount scaring away potential tenants or recommending a deflated rent amount causing less of a return monthly- Physically showing the home to potential tenants- Collecting/depositing monthly rents and bill paying- Vetting/screening applying tenants or managing non-paying/troublemaking tenants- Resolving maintenance repairs by hiring professionals to care for your investment - Turning your investment property move-outs quickly for new tenant placementLook for all of the above listed services and more when researching property management companies to receive the most return on investment!

We don’t know any PMCs to recommend in the 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.

In my previous life I owned medium sized businesses - very successful.  

Best ways to get tenant applications, screening tenants, collecting rent, banking, taxes (with or without creating a LLC), self managing the property and/or tenants, and everything else that comes with renting a place.