But, they will be in challenging parts of town where realistically you do not want to own property and your long-run returns will under-perform.I'd encourage you to find a balance of sub-market growth, nearby employment, strong income, and only then a good rent-to-value ratio. 

My wife and I live in Chicago and vacation in San Diego every year.  We get a condo rental in Oceanside typically, and stay for 2 weeks. I'm considering purchasing a condo or a small SFH in the Oceanside/Carlsbad area...

Research what properties or opportunities you’d realistically pursue if you sell.

True, there is tax court if they go against you, but for the most part that's not a realistic alternative.

That seems reasonable and realistic, especially given the parabolic inflation during this hold time. 

It sounds like you've been through a lot, but the fact that you’re jumping back in with a solid, realistic mindset is huge.

Realistically im probably at least a couple years away.

Would encouraging longer stays realistically help reduce this, especially for a medium-sized cabin?

Realistically I will get permitted in 2020 and be subject to the 2019 energy standards(solar).One door opens and one door closes.

After researching the basics, I am looking forward to understanding the realistic steps in concluding a first deal.