However, maybe due to bad luck, my experience with condos were negative, all due to HOA incompetence.When I purchased and moved into my Elmhurst condo, it was new, rehabbed from a aircraft factory.

Nonetheless I love my home but my next investment will be more strategic than an emotional one.

I am starting to believe that I need to learn the tax laws myself since I have lost so much money paying unnecessary taxes because my previous CPA's are not familiar with all laws or they just plug numbers into a software (without strategizing) and then I get hit with huge tax bills that could have been legally avoided. 

If you keep in mind all the aforementioned and you understand/respect the culture, being very strategic and resourceful there is a great chance you will land on the good side of this.

It requires being extremely hands on, otherwise you will go in the negative real quick.My advice would be to park 50% of the capital into something safe like a mutual fund and that invest the other 50% strategically into several passive opportunities.

1) Tax Harvesting with the Sale:Tax harvesting involves strategically realizing capital gains and losses to offset each other, reducing your overall tax liability.

Part of the answer may lie in the Mayor's Strategic Vision.  

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

Definitely check in with my strategic lender since 2003 @Joseph Chiofalo they have some exceptional FHA programs and he is one of the best in the business.

We are looking at maybe asking hard money lenders or private money lenders if they’d want to come on as strategic partners, but we need suggestions.