I like where your head is at, Eliot! My advice is to get connected with a realtor here in Bigger Pockets who is familiar with investing and househacking. It would definitely be worth looking into something like an FHA loan with 3.5% down to keep the remaining money that you budgeted "liquid" for your CapEx fund.
A lot of people get scared by HOA's, but they can be incredible value! They keep the common areas tidy and safe, as well as taking care of maintenance and care of common areas and exterior as you may know. For example, when it comes to CapEx (like you mentioned), you can focus what's going on within your 4 walls because the HOA budgets for the roof, siding, plumbing, etc because it's all common among the other condos.
As you likely know, all that matters is that your PITI (principal, interest, taxes, insurance) are covered by your collected rents. Rentometer and Craiglist will give you the most accurate figures for that.
Message me, and let me know how I can help!