Illinois just legalized recreational weed, however some of my tenants have been smoking it in their apartments long before legalization was even a consideration. 

-Am I willing to reinvest my cash flow into the properties and scale my portfolio before drawing an income?

Prices are still considerably higher than just a few years ago.

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.

Yes - I spoke with Ivan Barratt several years back many times over the course of a year, and put considerable efforts into due-diligence.

At least I am drawing my conclusion from my knowledge of algorithm, higher education and real estate experience on top of handling thousands of guests and residents with my own hands. 

It's also nice because we can upload invoices, quotes, drawings, permits, etc all to the individual project we create.

I love Cross Country specifically because they can service their own loans meaning that they handle all the construction draws and payment processing.Plus, I like Homestyle over 203k because they don't have as strict of guidelines on what has to be renovated.

How do you balance these considerations when choosing a location? 

We were so busy surviving, legacy building, financial planning or investing never came up for consideration (for most).