We have rented to some first-timers, but even most of them were older, less traditional students.

Roth or traditional or combination.  

I’m guessing the ski community is highly seasonal and has deep-rooted family traditions of return vacationers.

Financed through two traditional 30 year mortgages.

Most traditional RE Agents don't have a list like that.If anyone interested, i can expand how it becomes easier once you have your license.

The other is a non-traditional offering (higher risk and ideally higher return that even with some large issues seems likely to hit the high returns and is very frank about the problems they have encountered).  

For curiosity I asked Co-Pilot about it and got this response:The language in your CC&Rs stating that “no business or bed and breakfast is allowed” can indeed impact the interpretation of short-term rentals, but it may not be as straightforward as it seems.Definition of Business: Courts have often ruled that short-term rentals (like those listed on platforms such as Airbnb) do not necessarily qualify as a “business” in the traditional sense.

If you’re considering holding multiple properties, managing cash flow within the account to cover these expenses is crucial.If you convert a Traditional IRA to a Roth IRA, be aware of the tax consequences, as the conversion amount is taxed as ordinary income.

It is cheaper than the traditional cable box plans.

 You may be able to secure higher leverage financing through alternative lenders than a traditional bank (not always the case) and this may help advance your objective of reducing the down payment/cash requirement but that may only be temporary relief as you will likely pay more over the course of the loan because of higher rates and fees.