I'm not ready to compromise just because the market has gone insane-still want a quality property that throws off lots of cash.

If a deal doesn't meet your standards to accomplish your goals, don't compromise. 

That seems like it could be a good compromise, but I'd still have to feel comfortable trusting them with the renovation.Do you (or anyone else) have any thoughts about this? 

Maybe "owner-occupied rental" is a good compromise? 

I am working with a tax accountant to apply for a offer in compromise but  the results of that wont be known for at least a year. 

Downside is compromising on the size of the primary residence.

It’s also normal for them to take awhile, boards usually only meet once a month and that is when they approve/disapprove unless they have designated people.I’d suggest compromising that you will give the security deposit now and the first months rent when a move in date has been confirmed and in writing.

My wife wants to purchase a SFH and I want to build rental property portfolio, so it seemed like a good compromise could be a duplex where we could live in one unit and  rent out other unit while building some equity and updating the property. 

You're on the right track, don't let peer pressure from your friends compromise your financial future.

Member Planet: not HOA-specific per se, but like Wild Apricot offers a ton of functionality in the free tier with compromise that they're showcased in a rather overwhelming and dated "kitchen sink" interface that's not mobile friends and a steep learning curve to get off the ground.