Is my thinking correct that homes in highly appreciated areas won't benefit as much from Cost Seg. 

These tend to have less management headache but still have strong returns and tax benefits. 

I do like the tax benefits and leverage.

I would recommend an STR for the best tax benefits and cash flow no doubt.

I obviously want to get the best tax benefits and write off the expenses for the house and repairs I have done.

STR seems to have better tax benefits (in the right market) but is it worth it at a distance ???

But in reality, for younger people with moderate income, I actually see less benefit to financial planning.  

Slow start but hoping to gain momentum.

If you divide that amount into the capital gains tax savings, you'll get a number of months you'll have to own your current home to make the interest savings exceed the capital gains savings.

Rentals generate passive income, so an S-Corp offers no added tax benefit.