Their new online system is really confusing, and I have had to call customer support for help each time I needed to wire/ACH funds because I could never figure it out on my own (and their customer service chat box isn't set up yet). 

Quickbooks online could work for what you need.  

Buying your first in Jenks was a solid choice.

Find a local property management company that does the bigger cabins and they'll help you identify the right build choices to help maximize your rents.

These sellers can be more critical of everything you do i.e. the property description posted, choice of images to upload, frequency and time of open houses, negotiations etc. 2.

I don't care what anyone online says if you live there and have tenants at your home it will be a job. 

A good tip is to reach out to contractors, visit local supply stores, and check out online resources for cost ranges.

When I did an online search for commercial multifamily lenders, most have a minimum lending requirement of $1M and I don't need that much. 

Are there any good resources online to be able to get an idea of average monthly/yearly expenses like utilities, etc. for a given zip or city?

The only way to answer that in general (whether house hacking in today's market is still a good option) or for a particular property, is to learn how to run the numbers and analyze a specific property to see whether it will be able to stand on its own as an investment when you move out someday.There are a lot of resources here on BP for doing that but I'd just say, make sure the assumptions you're putting into your spreadsheet or deal analyzer are realistic.Make sure the rents (especially for vacant units or pro-forma #s) are realistic by doing your own rent comps; make sure the mortgage rate is realistic by doing some research online and/or talking to some mortgage folks; make sure insurance #s are realistic by getting a couple of quotes for the # of units and zip code / area you're looking in; etc.I hope that helps, and good luck 😊