Extremely expensive to have custom, fabricated spiral staircase and installed.

I would love to find other friends to live with me after they move out because it means I practically live for free collecting rent, but I'm struggling to find friends who would be willing to move in with me in my natural network.

Hardwoods given their nature just dont have the amount of BD ft in them so you need a LOT of them like Acres and acres to make it financially feasible.. but it certainly can happen in your area for those that own 100 acre plus or have some older growing pine etc. 

There is no one-size-fits all rule about best investments.If you know rentals, flipping, or lending, then focus on that area you know best.There are considerations about keeping things at arm's length, choosing investments that are passive vs active in nature, and some tax complexity around the use of leverage that require some guidance from a professional but can still be very profitable.  

Are there any Milwaukee investors that only focus  on cash flow or is the natural progression to seek appreciation after reaching your cash flow number?

However, there is a case for RV parks that more closely mimics a MH park when the location is appropriate for a full time living solution.The nature of RV parks can also vary across a wide spectrum.

Naturally my sights go to wholesaling, as the prerequisites are attainable within my allotted window.

Is this a natural progression in the business, or something that should be kept separated?

You also need to be aware that custodians are passive in nature and simply process transactions at your direction.

I am analytical by nature and have bouts of anxiety.