Are there any red flags or challenges specific to this neighborhood that I should keep in mind?

By keeping these principles in mind, you can optimize your position in the market.

As all of you can imagine, the questions that are running through my mind are never ending. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I think there are two maybe 3 ways to look at this in my mind.  1) you go into it and bring it all up to modern standards but using that old charm to basically take what is there bring it up to modern standards and rent it out essentially I'm thinking cocktail bar or something trendy like that.2) most banks are on really good centrally located real estate if this is true, then I'd consider it for the dirt, plan to scrape the lot and go vertical with whatever the highest and best use is.3) a kind of combo of the two, if the lot is in a good location and its doable, pull the vaults or other "character pieces" out of the building, scrape the lot, and build whatever is best suited for the site there, but incorporate those historical pieces into the final designs.Is the site near a major retail area? 

Most other costs are relatively standard I believe.  11) buy at market rates - dont splurge in a market because numbers look good - we are more than likely going to see balking in prices - if not a little recession in the next few years - would suck to own something you couldnt sell becuase you bought the most expensive property at the top - goes back to being mindful of your market.  

You can research these online.

No matter where you choose to invest, please keep in mind the following (copy & paste):--------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

Check online reviews and interview multiple contractors to compare bids.

I wouldn't say you're going to learn as much going through an online course as you would an in-person one, but it is a lot more convenient.