Ideas for some of the paragraphs: - Future Setting: where you live, what you see from your front porch or backyard, what your kitchen/gym look like. - Family: Kids? 

A high property tax rate will increase the taxes more quickly as a percentage of total expenses when the property value increases.

Walking through, I can see that owner is the type that spares little expense with his own properties. 

I talked an experienced investor and he said $300 to $400 for San Francisco - the insurance company is going to go with the less expensive costs.

Co-living is going to grow and grow as time goes on (but maybe less so in my neck of the woods, to be honest).

And someone jumping into this as a complete newbie can expect that they have a decent chance of making some expensive newbie mistakes.

I would recommend finding a way to continue to practice in some capacity, at the very least to cover living expenses.

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

I lived in LA for a decade and we have many friends, family, clients and community members suffering and send our sincerest condolences to all of those experiencing and affected this tragedy. 

Flips have done good not great, Air Bnbs are going good not great, and rentals all were brrrr'd perfectly but like most cash flow just enough to pay the bills and cover expenses.