Seems to me that a 3-month stay is actually pretty nice because you don't have to think about anything as a landlord for three months but it's also a simple cleaning when they vacate.

The market in this area is pretty strong with quite a bit of population and job growth, near good schools, etc but in a relatively older part of town.

Having a simple written agreement of loan terms and responsibilities of the two parties is always nice and it doesn't have to be from an attorney just something clear that you both understand and agree to with a signature.

We do have some really nice resorts that offer these, but there are too many negatives for what investors will typically put up with. 

I especially recommend it if you are building the empire while having a W2 job.

Each participant in her program has to commit to going back to school/job training and she works with them to improve financial literacy and grow their income.

I've heard of people using classes for each property/tenant, but I've also heard of people using customers or jobs for each property/tenant.

In addition, my W-2 job is entirely remote.

@Schuyler Covert Focus on establishing your job, income history, credit, and savings account.

Typically, it's applicable to certain types of property, and the rules can change.Regarding short-term rentals and bonus depreciation, the Tax Cuts and Jobs Act (TCJA) introduced favorable changes for businesses, including bonus depreciation for certain qualified property, but the specifics can depend on your situation.Using your property for short-term rentals may affect your ability to qualify for certain tax benefits, and the classification of your property (personal residence, rental property, business property, etc.) can impact the tax treatment.The IRS has guidelines regarding the depreciation of rental property, and bonus depreciation may not always be applicable to residential rental property.Additionally, if you decide to switch the use of your property (from short-term rental to long-term or mid-term rental), there could be implications for tax treatment.Given the complexity of tax laws and the potential impact on your specific situation, it is strongly recommended that you seek advice from a qualified tax professional.