Until then I had been doing it myself but he felt it was time for an upgrade.

I think if your property has upgrades that make it worth more you may just have to wait a little longer as it seems the overall rental market is taking longer.

Efficient Renovations: Focused on high-impact upgrades like modernizing the kitchen and bathrooms, improving curb appeal, and installing energy-efficient features, which are highly desirable in this competitive market.Optimizing Layout: Evaluated the property's layout to ensure it met modern buyer preferences, such as creating open-concept spaces.

As far as I can tell Airbnb does not yet offer that capability in Hawaii.I met with a few agents and cleaners while on island and their feedback was that it should be cash flowing nicely without any major repairs or upgrades.

Efficiency Maine has programs that offer rebates for multifamily upgrades: https://www.efficiencymaine.com/at-work/multifamily/ .

I’m also currently looking to upgrade to a software that allows me to transfer friends from PM to owner and will help me generate form 1099at the end of the year.

Half the time, the course is like buyer beware, sorry, let's try an upgraded program for you.I think seeing the posts and votes can help new people to the "family" discern at least who has been here for a while and who is assisting others.

(I think this is realistic because many property with the same sq footage in the area with upgrades are going close to 600K).

I would expect start-up costs such as stocking linens/bedding, upgrading certain furnishing and amenities, and pass-through costs for listing on the OTAs (like VRBO, Airbnb). 

With the right maintenance and upgrades you could sell it for a decent profit after.