I'll say it again, we are not looking at this as an additional source of income.
We may rent it out ~March through June because why not, but we are not expecting rental income. Like I said, we'd purchase if and only if we're ready to take it on without $1 of rent coming in, which we're close to doing.
And like in the OP, I'm interested in people who have done this (like Lax, apparently). Not the chicken sh!ts like wiz who give advice out of their mom's basement.
OK but you also said -- "Where do you get started trying to understand what you can get for airbnb rent?" and "But we still want to get into a place that maximizes that rental income."
So here are the things you really need to nail down:
1. Is this an investment in an asset where you are looking to see a return on that investment either through rental income or appreciation?
2. If the answer to #1 is yes, what are your goals? $X/month in rent? Y% appreciation over Z years? You want to model all of that to determine how much you're willing to spend. Typically, you can determine expected rental income by looking at comps on VRBO or AirBnB and then talking to owners about the occupancy rate during "peak season." Alternatively, you can look at comps on VRBO and see when they are booked to determine a rough approximation of the occupancy rate... but you are best off talking to people or management companies for more accurate numbers.
3. If the answer to #1 is no, and you really want to focus on it being a "family vacation home" then you need to evaluate the following:
3A.
Accessibility. Directly affects how much you will use it. Driveable? Easy/cheap flights? The main reason people don't use timeshares, vacation properties, etc. is how hard it is to get to them.
3B.
Affordability. Does the constraint on your finances preclude you from doing other things? Does it preclude you from taking other vacations and are you OK with that? What are the financial risks associated with the purchase and how may they affect your "normal" life?
3C.
Purpose.How do you envision using the property in the short term? What about the long term? Is there any extended family that would use it? Why *this* place and not another place? What is the exit strategy, if any?
IMO, the most important thing is finding a property that is financially viable. Ideally you want to be able to pay all cash, if that's not realistic you want a mortgage that is not more than 50% of your expected "rental income." There are so many costs associated with a property beyond HOAs that you need to mitigate your risk of taking direct losses on the property. After you've figured out what kind of property will be financially viable from an investment/rental standpoint, make sure it is accessible, affordable (i.e. taking vacations there will not "put you out"), and serves a purpose for your family.
For our property, it checked a ton of boxes... beachfront (so long term that's great for kids and aging adults getting out there with minimal difficulty), great golf and activities, driveable from primary residence in Virginia, very close to Charleston for flights as well as going into the city... and then financially the equation worked. Don't just get something to get something, get something that fits specific goals of yours and fits your family.