Not all designers understand vacation rentals.

If you're looking for appreciation and are comfortable with being a landlord, keeping it as a rental could work, especially if it's cash-flowing $300/month.

A feature that our Pro Members love is the fact that they can manage of all their rental properties for free using RentRedi.

Congrats @Emily Pena - I'm also an agent (working mostly with investors), property manager and an investor myself (currently owning 26 rental units). 

for fix and rental projects or for fix and flips?

Outside of that, looking for value add opportunities that help maximize rents and understanding immediate needs to turn it over to the a rental (appliances, fixtures, paint, flooring, etc.). 

There is around 500k equity in the property. 150k-200k would get the property fully rented at top dollar with desirable tenants. 100k would get it to where I can rent all the units back out at fair reasonable market rents.

Begin by educating yourself through books like The House Hacking Strategy and podcasts like BiggerPockets, and join online communities for support.

That likely means that they are not good with money management which you are likely expecting from him.To answer your question, if you are doing long-term rentals, the LLC taxed as a partnership is likely the go to route.Best of luck.  

After 12 years in the furnished rental game, I'd say that is a pretty good sample size.