[Minnewaska]

Denise, the plan sounds fine. It seems that boat expenses are causing real stress for you. Why not sell the Oday and get a smaller day sailor, without systems? Maybe even a trailer sailor, if you have a place to put it at home. I've always thought a 20ft cat rigged boat with a small cabin with porta potti would be a terrific trailer sailor. This assumes you still wish to be sailing.

 

[Minnewaska]

Being disappointed in oneself is a self inflicted wound. You are the judge and jury, pardon yourself. You own a house and boat, which literally puts you in the top 10% or 20% of wealth in the country. Not so bad. You know that nearly half the country has a nearly zero net worth? Settle into a program where you can be happy. If you love sailing, just pick the spot you can afford to eliminate the financial stress. You will enjoy it more. If you don't, find something you can enjoy. If sailing reminds you of a lost dream, nothing wrong with finding another avocation. Maybe get a part time job in the marine industry (West Marine?). A little extra spending money for the boat and probably access to good discounts. Good luck.