To move away, we either cut our lifestyle in half or figure out a way to give our portfolio a "make-over" to somehow squeeze more profit out of it while at the same time hiring management so that I don't have to work on it full-time..I'd love to hear any success stories of others who have been in our shoes or advice on what direction to take. 

You're not likley to find someone on this site to cut you a check.  

But investing anymore in getting old ones back VS just buying new would be in my opinion a waste of money.

If you need to do any convincing, or pushing they are not motivated and a waste of my time.We rank #1 on Google for pretty much any keyword you can possibly imagine, and people that absolutely need/want to sell find my website, see how good looking I am and fill in the form.Because they are motivated we can get them for a severe discount, and still make the seller happy.Win for everyone.

But another driver is overall cost-cutting.

I have been a little shocked that about half of what I got is telling me I am wrong or that what I have already done is a waste of time. 

I want to purchase more properties next year and I plan on switching to a higher paid job plus I will be cutting my expenses by renting out the other side and having a roommate (I have a FHA loan).

The 2017 Tax Cuts and Job act allows you to fully depreciate those assets in the first year of owning the building rather than waiting and depreciating them over their useful life.Example: Let’s say you purchased a building for $100,000, you could deduct approximately $30,000 immediately utilizing the 100% bonus depreciation rule.

The best thing for your brother is cutting the cord ASAP and making him survive on his own. 

All the best in the business cut their teeth on some learning lessons to the top.