Keep in mind too, a 20 year ground lease is not considered long term. 

So my first step is finding and meeting others in the area that are like-minded and share the same goals. 

Keep in mind, if you close on say the 2nd of the month, your mortgage won't be due for almost 60 days.

@Christian Tibok The last short sale I did had the 1st offer $3,000 to the second, which they approved.About 4 weeks before closing, the 2nd changed their mind and said they wanted $8,500. 

There are so many great resources on this site, so keep learning:Attend local REIA meetings and connect with like-minded investors: http://www.biggerpockets.com/meetRead the Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingListen to the BP Podcasts: http://www.biggerpockets.com/renewsblog/category/podcast/

Do you mind sending me an email or giving me a call or providing me with yours so I can send you one?

For what it's worth, it will not be our primary residence until years down the road depending on how things go (when we "retire"), but it sounds like, regardless, we should steer clear of both options (LLC and fancy self-directed IRAS) unless we want the LLC for pure liability peace-of-mind if we did somehow rent out the land or a structure on it (if it wasn't our primary residence).Thanks again for taking the time to reply, still figuring it all out and this really helps.

When in a small, highly peculiar town, it's actually more efficient to ask our regional network.Plus it helps show factual like-minded teamwork.

, maintenance (beyond what the HOA covers), and property management (if you ever decide to no longer self manage) - you may be losing more money than it initially appears.HOWEVER, the Beverly area is on fire right now, it is completely possible that property values will continue to climb quickly, and you could exit your condo in ~5yrs and make a nice profit (keep in mind you'll have paid closing costs once as a buyer, and once as a seller at this point, which will really eat into the profits if, say, you bought at $250k and sold for $300k - not a straight $50k profit, plus you had negative cashflow over the years too).So...

I hope you do not mind.