I Believe that you should always raise the rent even if only a little bit that way the tenant consistently gets used to it and will not get comfortable with their current rent.

I would feel very comfortable that ordering a full appraisal would show the value closer to the $183k value.

If they are comfortable with being in the stock market and 401ks give them the best options that you can in that space.

One that fits at least 7 people comfortably.

I have also worked as a real estate agent in the past and have more recently worked as a project manager for a flipper in the area, so I have general knowledge of different aspects in real estate and feel comfortable with most of the processes associated with it. 

Find a nice, small multifamily (2 - 4 units), in an area you want to live (with some appreciation), with as much or as little reno as you are comfortable taking on.

Hopefully, the inspection goes well and I will own a property that a HML will be comfortable with.

who knows, but I would like to begin framing myself for a very comfortable retirement. 

As an app state alum I see that last pic and want to immediately go relax on your porch.

That was just a little more comfortable for me and allowed the house to cash flow better.