We do coach the ones who have not owned a home before about little things and they sometimes ask us questions but we are mostly hands off...

If I need cash I can sell stock and transfer it.

Basically deed it into the Corp, most likely pay the transfer taxes and be done.

Option 1: invest in multi family housing Pro- semi reliable income- cuts cost on my living expenditures -recession proof (can be argued)Cons- high cost start (for me at least)- first time managingOption 2: Buy land and try to negotiate a development deal Pro-huge reward -can be fast- after deal is done right, I'm hands offCon-very risky especially for intro-no expertise in this field -finding a great deal in hardOption 3: wholesalePro-great return-can be fast-not long term Con-hard to find good deals especially with a full time job -can be a nightmare project-no expertise Please correct me if I have messed up with any of my pros/cons.

If you run a tight ship I think you can make it work as long as your local and hands on.

Both SFRs and Multi's can be great rentals.  5) Manage this second one yourself to see first hand the complexity, but then plan on hiring a property manager for #3 and #4 after you get tired of whiny tenants. 

I'd be willing to move a lot more money over if we were going to be using their lending services.We have been using Fortera but their online system is TERRIBLE, especially for trying to transfer money to and from our Ally accounts. 

I've networked with an experienced flipper who found the deal and proposes I finance the job, he does most of the work and manages the subs and I take up the painting of the house and lend a hand with some labor. 50/50 split on the exit.  

I've narrowed down to a handful of areas, and on paper Fort Wayne seems like it's full of potential opportunities.

I transferred funds from old 401Ks and IRAs to the custodian and I have them invest those funds into two IRA LLCs.