Asking in the correct forum will get a better response.Read the RULES!

Hopefully we get some better virtual furniture in listing pictures lol

2-If we need to issue 1099's, we can use my wife's SSN, but would it be better for privacy if we use EIN?

The key takeaway was timing...selling each property in a way that allowed him to hit the 45-day identification period without rushing into a subpar deal.In your case, with SFHs in Jacksonville and Ocala plus that duplex in Port Charlotte, I’d look at where each market stands right now and figure out if there’s a single buyer who’ll pay close to fair value for the whole set or if you might do better by splitting them up.

A primary residence will most often provide more favorable loan terms so if you are willing to wait one year while you living in your new property and are comfortable with renting out your primary residence to a tenant, then getting something such as an FHA loan is a good strategy to minimize your upfront costs and hopefully get better loan terms.

That may be a better use of your time and resources.

Their advantages include house hacking which includes better finance options and hustle.My last purchase was so large cash negative that the rents were $3k less than PITI.  

I'm also working on upgrades for THE MTR Connect - better scheduling, automations, guest speakers, social media - all to help promote the collaborative and supportive space my colleague @Jamie Banks and I have created.

I'm sure there are things we can do to get better and we'll use this as a learning opportunity.  

The importance of grasping real estate principles, finance, and law cannot be overstated but often are ignored because someone spent a weekend at a seminar.