@Camille Romerounless you are able to spend some significant time in your chosen location in person, and work on building a network there, i would pick a market closer to NYC, within a couple hours.  

Ask to see the approved final site plan for the first phase.

It's possible to buy property in Germany with as little as 5-10% down, making it an attractive option for service members and civilian government employees stationed there or planning to settle.

Instead of continuing to hire remediation contractors you should hire a hygenist to come in, do some testing and provide a remediation plan.

I’m planning to start by buying in Buffalo to gain experience and learn the ropes.

Quote from @Gamal Harding: Anduril Industries' Expansion to Columbus: A Transformative Move for Real Estate InvestorsAnduril Industries, a prominent defense technology company based in Costa Mesa, California, has announced plans to establish a new manufacturing facility in Pickaway County, near Rickenbacker International Airport.

All this to say they are getting serious about permitting so if you are planning to invest in San Antonio in the short term rental space, MAKE SURE to check that the property is eligible for a short term rental permit given the density limits above and have a Realtor experienced with the San Antonio permitting requirements and rules. 

I am also leaning towards GC'ing it myself, so I'm using an architect to draw up plans, and I'm looking for subs.

So this involves hiring an architect draw up plans ($1,000 - 3,000 if I had to guess).  

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.