I have a STR but am knowledgeable about many other strategies and plan to pursue a BRRRR as my next investment. 

Obviously there will be a fee a pay for the services of course but i’m noticing most CPA are trying to sell me a packaged deal meant for REI who have larger portfolios with complex tax planning/strategy needed and I haven't found someone who fits my need.  

Might be worth taking a look if you are planning to make a switch.

Both can be sound investments and strateigies, its just a matter of understanidng the proper business plan and execution.

Back then it was part of my retirement plan.

For management, I'm guessing you plan to self manage.

(But you'd likely be limited by HOA - as far as which days and hours you can make noise in it remodeling)If you do stick with the plan for buying in the Loop, and have access to cash, whether yours or you borrow.... family, hard money lender etc...

Since you want it to be as easy/quick as possible, I'll give you three things you need to learn...as a starting point:1 - How to Analyze Markets to find the Micro-markets that are good to invest in.2 - How Money Works, so you can develop an unlimited number of strategies which will allow you to be able to take advantage of as many opportunities as possible.3 - How to design your own REI Plan by reverse engineering from your specific set of financial goals back to where you are now...then execute it by turning around and just following the breadcrumbs.4 - (OK, I said it wasn't as easy as "just one thing")...Learn what the meaning of the number sequence "1073751824" means, and how to base EVERY decision you make on the meaning of that number sequence.5 - Learn why it's so important to follow the 2 Golden Rules of REI, of which GR#1 is:  NEVER, under ANY circumstances, ever, EVER, spend your seed money (your starting cash). 

Investing in this market is not a cake walk, so ensure that you talk to a number of folks and begin to formulate your plan of action moving forward.

How long are you planning to hold this property?