Consider Tiffin.Des Moines offers even more options because of its size and spread.

Because of my professional experience, we'd prefer that our properties be nearby so we can self-manage and save the 5-8% typical of property management fees, at least until our portfolio grows.

The Issues between tenants and landlords typically are handled at the county court level.

Typically HELOCs are used for short term purposes, so it would make more sense if you are doing a flip.

I see value in both, but I'm unsure which is the better option.

I prefer to utilize a broker lender because they generally have access to more unique loans, however I do know some BANKS or credit unions have inhouse portfolio programs available that don't exactly follow fed guidelines, which may also be good options. 

Now that I am older and have more options I recently started learning about real estate on youtube and it led me here, BiggerPockets.

I mean once you talk to them, it's pretty easy to spot if they know what they are talking about.I've work on STRs before and to be honest, it is not the most fun aspect of accounting because the volume of allocating income from all sources (airbnb, vrbo, stripe, direct booking, and so on) to a bunch of random expenses (cleaning, supplies, repairs, advertising, commissions, and all typical real estate expenses).I had to strictly rely on the client's input on what the expenses belong to which property or even units, if the paperwork doesn't say. 

I have a buddy that is in mortgage but unfortunately we are not able to secure deals with his company because most buyers have better financing or cash options and this is taking me out of the game.

Secure funding for your flip through options like hard money loans, private investors, or leveraging your home's equity with a HELOC.