Ultimately, it comes down to underwriting and the ability for the property, and you, to afford to pay the monthly expense of the loan. 

You've got to include loan pay down, appreciation, and depreciation in your return calculations.The point of cash flow is to keep you safe.

Your first year will be a learning experience, you will want to be close to the action, as you may not have the capital to pay someone to handle everything.

Right now you have $1,000 in cash flow that can be used to fund other projects (seed money), pay you in profit to supplement your lifestyle, or fill in any gaps for underperforming properties.  

That's disappointing, I'm here to learn and would happily pay for it if I used it extensively.

Someone told me I’m crazy since they still always pay. 

However, with the rates and conditions of any triplexes and fourplexes we could find (we did find one, but it's in the Pendleton Heights suburb of KCMO, so we were worried about it being too dangerous of an area), we were wondering if it's worth it to buy a duplex and rent out the other half to help pay the mortgage, or if it's more worthwhile to rent an apartment and try to save up to buy a residential or commercial MFH later?

You are going to pay more for something new so you might take a look on the local Craigslist, FB marketplace or OfferUP and see what is out there.

However, chances of making a mistake or overlooking an opportunity to save are higher when it comes to rentals.The dilemma is whether it's worth paying a professional in this case.

So I proceeded to pay for four appraisals that were like $800 apiece.