One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

Since my tax guy is of no use, I reached out to a friend who works for a different tax group/CPA and this new firm was kind enough to look into my predicament.

Baltimore City is tenant friendly and very hostile to investors.  

Hmmn.. maybe you should actually advise your pre-Covid operator friends to stop churning out Covid syndicators from their boot camps like it’s a pack of cigarettes.

Always great to make new connections and friends.

Given your experience managing 138 doors, you already have a significant advantage in understanding tenant needs, property maintenance, and financial planning.Key tips:Focus on personal finances: Keep building excellent credit and maintaining healthy reserves.Financing: Explore loan options like conventional, or DSCR loans to maximize your purchasing power.Location: Research neighborhoods with strong Section 8 demand and landlord-friendly regulations.Due diligence: Analyze properties carefully, factoring in rehab costs, property management, and cash flow potential.Your expertise and willingness to learn put you in a strong position—best of luck!

If you both are on the title (you/husband + friends' LLC) you'll both have to agree about whatever disposition.

He abandoned it during his demon years so his best friend took it over and added a couple more people before it desolved due to all going off to college.In college he had a side hustle of finding things on free sites, putting them up for sale, selling the free item and offering to transport it for a modest fee.  

What are things I should take in to consideration on my first deal.Would love recommendations for investors friendly agents and property managers.Thanks!

I'd try to understand landlord laws in each market - i.e. figure out which markets are more landlord friendly.