AI and tech are helping loads with attracting guests and streamlining efforts in management.

Converting your STR to a primary residence for 2 years can help avoid some capital gains taxes under the Section 121 exclusion (up to $250K or $500K if married), but it won't eliminate depreciation recapture.

I just want to help and build something that is useful.

Very helpful, thank you John! 

Make sure your listing is SEO optimized with the right keywords to attract more renters—many property management companies can help with this, along with tenant screening and payment management.

@Don Konipolthank you all for the responses, very helpful.

In your case, since your parents own the properties and you’re helping them out, you may not be able to claim those deductions unless they pay you for your services.

Even moving to a MTR fully furnished rental could help..

It may help you dispel the myth that people with disabilities are a bad risk, undesirable as tenants, or are likely to have undesirable service animals.In some jurisdictions, you can't discriminate on "source of income".

Hope this helps.