Worked out pretty well for me ;) Russell how did that appreciation work out for you.. that icing on the cake  that luck .. that gambling.. how did that all work anyway.?

Maybe she needs 3-6 months of your usual expenses in savings before she can feel comfortable with you “gambling” for your future goals. 

Hard money lenders stay in business by making smart investments in people, not by gambling their money on anyone who wants to enter the business.Good luck!

So it's a gamble.

The stocks to me are similar to a gambling

Roommates are always a gamble but usually more profitable. 

Your equity is in jeopardy in a SFH at this time.Others will have a opposing opinion but do you want to take the gamble of holding if you already know that you have likely maximised your appreciation for the foreseeable future and risk a market/equity drop.

I have a dog, I believe my wife and I are responsible home and pet owners yet it has damaged my property.Being a responsible pet owner does not prevent animals from getting sick, throwing up on carpets, having accidents or bladder problems or other uncontrollable damage issues. 

I want the appreciation play and if you study the trends carefully it is not gambling just like the last 6-7 years .

I wouldn't want to gamble on a foundation and end up spending tens of thousands to fix it that was not expected.