If it sucks for you, you can sell and be further ahead than you already are today.

Would need to know a bit more before giving a specific direction but it is usually best to hang on to your property and not sell whether you expand on it or rent it out and purchase a bigger property.  

It is slowly rotting and needs significant repairs to get it prepared to sell to a typical home buyer for a primary residence.

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

You are unlikely to sell all the properties to one buyer.

Based on your description, Party 1 seems like the safer choice.

Although i do think there is more money to be made in RE than selling soap. 

Hard to give good advice without more info, but since You are single no kids it's hard to beat buying a single family fixer upper and living in it for two years and then selling for tax free profits....I'm a big fan of Waltham these days $.02 

I believe this tough-on-crime approach will make Albuquerque safer and a better place to do business in the near and long-term future. 

And selling real estate is usually easier than selling a business.