However, that area is still very much in transition so unless you're comfortable investing in C-D- areas, make sure you have an agent who is very knowledgeable of the neighborhoods to steer you in the right direction. 

Are you comfortable leveraging more in 2021?

In my market 5+ is considered commercial and lenders won't do VA in that asset class.  1-4 is doable here via VA.If your reading and studying has given you a good comfort level, most definitely jump in. 

There are many options you can take to progress, but it really depends on your comfortability and goals.

I want to maximize my cash flow for that first year and if I have the space available to me then why not.

Very experienced investors or people with a lot of construction experience are sometimes comfortable doing their own “inspection” on the initial walkthrough.

At $844 mortgage a month I'd be much more comfortable.

If you are less comfortable living with people, I’d suggest going straight for a duplex-triplex and then live in a side for a year, rinse, wash, repeat.

Basically how do you maximize your return in this situation.

Yes I am trying to max my leverage as well as maximize on my cash on hand right now which currently is enough to payoff property 1.