I don't think we meet the requirements for a Schedule C business. (I don't know what they are).
Then you need to find out what they are. I *HIGHLY* suggest you get with a CPA or tax pro in your local area for clarification on this. *IT* *MATTERS*!!!!
For SCH E Rental Real Estate start up expenses are flat out not allowed. Period. Not one penny.
But if you're doing "vacation rentals" on AirB&B that sounds more like a hotel operation, than a long term rental operation. Now that *would* be a SCH C business. Basically, one of the requirements is that you must provide your tenants a service that is directly beneficial to the tenant "on a recurring basis". For example, making the beds daily, offering a weekly linen service, offering laundry service, etc. Understand that does not mean that you personally have to provide those recurring services. You could contract them out to a 3rd party if you want, or have AirB&B take care of doing that for you, if offered.
Additionally, you need to know some definitions as clarified by your state, county or city. One clarification needed is what constitutes a "short term rental". In my city a short term rental is defined as any property that is leased out for *less* than 30 days for any one period during the entire calendar year. So say I rent out a property for Jan-Feb to a tenant, then rent it out for 2 weeks only to the next tenant, and then rent it for the rest of the year to a third tenant. By my city's clarification my rental property is treated like a short term rental for the "entire" year. My city imposes a $3 per night - per person bed tax on all hotels, hostels and short term rentals. That would mean I would have to pay that bed tax for every single night my property was rented for the entire year, and that's $3 per person, per night.
So get with a tax professional in your local area to ensure you are following all the laws, rules, regulations and ordinances of your local jurisdiction.
The last thing you need at your retirement time, is a hefty amount of fines and penalties for not following some obscure law, regulation or ordinance. So please seek professional advice from a local pro in your area that is well versed in the laws and ordinances in your area. My bet is, you do have a SCH C business where you can deduct your startup costs. But the last thing you want is to have those deductions cancelled out with fines, penalties and back taxes because you didn't collect and pay something like a simple bed tax.
