There are a lot of questions I would have prior to offering any advice, but it sounds like something you can structure on the surface. 

Also, on the surface, many properties look like they'll cashflow per 1% rule.

Two cleaners, plus my wife and I and help from our 3 kids worked each day around the workers to clean, replace furnace filter, replace bulbs and batteries, mop and wipe all surfaces, throw out trash, move furniture, re-hang pictures etc.Don't think I want to do that again soon.

While the house hasn't given us any major challenges, given its age, who knows what could be lurking under the surface.

Quote from @Jonathan Ruths: It sounds OK on the surface.

If a guest made a reservation prior to you having a hurricane or weather policy in place, let them know how the situation would be handled before a hurricane or a bad storm arises.As far as prepping your property goes, I would recommend checking the following boxes at a minimum before a storm/hurricane emerges:- Have a plan in place to secure outdoor furniture and miscellaneous items- Trim trees & branches- Have a protection plan in place for windows and doors- Waterproof important documents- Put fragile items or valuables on elevated surfaces- Review your insurance policy- Check that your roof and siding is secured and not loose- Ensure you still have an effective way to communicate in the case that service goes out in the areaIf you do not live near your property and are unable to check these boxes, find a reliable handyman and/or professional that will be able to complete these tasks for you.If I am missing anything, please add your suggestions below!

@Tenzin Kalden buying very cheap properties is very tempting and seems like the way to go on the surface, but over time (for me almost 15 years) you realize that quality matters in the long run.

If most VRBO's do have a pool then make sure you have the proper insurance follow regulations (fence around pool etc) maybe even have an alarm on the pool that would buzz in the house if surface water disturbed like if someone fell in.Then have a professional pool company maintain it.

Investing in student houses looks great on the surface.

Most of the books barely scratch the surface and are little more than an intro, not enough to actually invest in them.