If it was me I'd sell Encinitas take the 1/2 mil tax free, keep the land in Carlsbad and build that dream home, and have a fun project with your mentor's home as a retreat.  

Another thing to consider could be that if the property is further north where winter weather can impact them then you may see buyers less willing to move then. 

Space & Rocket Center museum, over 60 public parks and the Von Braun Center entertainment complex, making it a fun and lively spot to raiseRead Full Story - HERE

Based on the supply of homes for sale and the time of year, I predict home values will drop a little bit over this winter until early spring.

Also to eventually own a home within 50 miles of the Aspen CO area (winter/employment location). 

Sounds like a fun property to furnish!

Sorry to bring this back to the opening post... it is great fun to read about all the ways the young people do things that "we" didn't.I mainly disagree with number 1.  

So with all that, I'm thinking to open booking now for next summer with a 7 day minimum, see how it books out, and by late winter/spring I can reduce it to a 3 day min to fill any remaining weekends, and then work on filling mid-week vacancies as summer approaches.We were leaning towards Fri-Fri, but Michael I like your suggestion about the Mon-Mon option, which could be nice because renters would have the weekend to travel and then begin their stay on a Monday, then they would end their stay on an upnote with a long weekend...But with either Fri-Fri or Mon-Mon renters would probably need to take 6 days off work...Sunday-Sunday might actually be better because renters would only need 5 days off.  

Fun question.

Let me tell you, when you’re “unemployed” and the rent coming in is the only way to make $15k/month in payments and pay your bills it’s “less fun”.