The roommates you choose should be compatible with your ways of living, and you should also feel comfortable living with your roommate.

I'm newly married, so now with a dual income household and split expenses, I'm starting to feel more comfortable about taking a step into investing in real estate.My original goal was to always keep my current home and rent it out regardless of where I moved next, because I think we could make $200-300 per/mo. on it (not including maintenance/vacancy) - and when the mortgage wraps up, even better.We're not looking to move any time soon, so I think our next step will be to look for a duplex in 2022 - hopefully near Bay View but open to other Neighborhoods in the Milwaukee area.

It is up to your comfort level, research you've done, team established and finding the right deal.

If I were in your shoes, I'd continue full time work at your W2 while building up your agent business on the side.  

while ready to buy when a good deal comes along I find myself waiting to see if the other shoe will drop.build - there is no one I am aware of doing any substantial construction of single family rental communities here in OKC. 

They would feel most comfortable in a senior trailer park that is also small-dog friendly.

If you’re comfortable with more than a SFH, do it.

We all have to leave our comfort zones at some point to learn new things and step to higher levels!  

However in the same state, you may have many closing companies that either feel it's illegal or aren't comfortable and won't allow it. 

While I own and live in New England and the housing market is very attractive, I don't think I'm comfortable with the amount of capital I need upfront for my first property.