My main concern is how long it takes to process deals after placing an offer.

There are so many options for Real Estate CRM's and many are not easy to use. 

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

On the other hand, if you want something simpler or closer to home, a single-family home might work better.Since you need more space for your growing family, consider looking for properties that offer both extra room and good investment potential.

When you have a pool deck full of residents and their friends, I can see real value.  

In the past 5 months, we have put in multiple offers on REO, auction, HUD, and Fannie Mae properties, without much success.

You can also offer to refi within "x" number of years so they eventually get the entitlement back.

PS: I can help you get two or three out-of-state properties in Alabama that will cash flow, and I could also provide DSCR loans for real estate investors like yourself in Monmouth County. 

My Landscape company is an S Corp so I am familiar with that business structure, but I just don't know the best way to structure a real estate company.

I already have an Equity Trust account with an old Roth IRA but they do not offer checkbook control.