Whereas with VRBO I've had several tech issues that were unfixable, such as photos that never load no matter how much I manipulate them, and a catch 22 with the dynamic pricing that never worked that locked me out of my calendar. 

Offering referral incentives could also attract interest if you rather not pay a listing agent's commission fee.Investor Meetups & Events: Consider presenting your property at virtual or local real estate meetups, particularly those that focus on turnkey investments.Online Listing Platforms: Sites like Zillow, Roofstock, and Craigslist (targeting investor hubs) can expose your property to out of state buyers.Professional Photos & Financials: No matter the platform, strong visuals paired with clear financial data (rental income, expenses, etc.) will help busy investors see the value quickly.

For example, if a tenant texts the landlord a photo along with a message saying, “the sink is leaking” the message and photo will automatically be logged as a maintenance request in the landlord’s dashboard without requiring the tenant to submit a formal online request.

The basement 1/1 with a hot tub stayed full and did well booking at the last minute so we kept prices higher there longer.

They may also be able to help you develop a scope of work for repairs and maintenance and can probably do the work as well.

My main concern is that my insurance policy is from when I was occupying, and I'd rather not have to get a new policy, one reason being that they made a huge stink about the downstairs tenant's 20-25 lb dog having minority pitbull DNA, which I eventually won the argument on after sending them photos, vet records, etc.

It would help if you had video/photo evidence of the traffic and share that with the police.

Quote from @Bruce Woodruff: Quote from @Ed Daniels: @Noah Kellar tough to advise without a photo, but I think the consideration about how it would turn out to repair and paint, remove siding to paint wood, or re-side is easy to me as an investor... whatever looks the best for minimum cost.  

3. how well have you marketed the property?

Well, now you are getting EXACTLY what you paid for!