Hi Shep34 and welcome to CF.
I may be in somewhat of a similar situation. I'm 55, single, and have been living here in
Egypt for most of the past 19 years. I have finally decided to call it quits in this country and return to the States permanently.
As I have no living
family I really have no place to return to stateside. From Louisiana, spent most of my
Navy career in Norfolk, Va. and have a few old
navy buddies in
Florida. I have lived aboard
boats in the past so I decided that since I didn't know where I was to reside in the States I would buy a sailboat and
liveaboard until I either grew up or figured out where I want to end up. So I have purchased my little 27-foot
pocket cruiser after the
boat received good marks across the board from the
marine surveyor and plan to sail around the
Chesapeake Bay and point further north and south for 6-months to a year living on my navy
retirement plus a little extra here and there.
I've done a bit of sailing here in the Red Sea on occassion but not enough to be considered an experienced single-handed sailor. I
repair private yachts here in the Red Sea and have owned
boats in the past so I have a pretty good idea about what will be required to outfit my new-to-me sailboat and the associated costs.
You asked about fears and failures. Well, I certainly have my fair share of fears...but no failures so far (as I haven't stepped aboard the
boat yet). Aside from my own fear of the culture shock that awaits me after not having visited the States in 10 years, my greatest fear is my lack of hands on experience at this point. That will change with time as the miles move beneath the
keel. Another fear is
hurricane season on the
East Coast. Have been through a few hurricanes and have seen the damage they can do. I fear losing the boat, which is my home, and having to start over yet again.
The only successes that I have had so far are that I actually purchased the boat, a plane ticket to the States, and have been given a
wheel autopilot and an
AIS and
GPS capable
VHF radio from my
current employer as a bonus for the
work I've done on his boat to date (Restoring a 1937 27-meter yacht).
So good luck if you decide to jump aboard and take the helm!