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? 

This also includes a few credit cards that are used for business expenses.

Depeding on the amount get a credit card that has no interest for 12-18 months. 

If i can invest it and make a significant better return after tax than paying it down I would do that but in this instance you will never be able to achieve returns that match credit card debt.

Next year i'll hit top pay and should start bringing in 1.2-1.3k a week. and the year after that i plan to move to linehaul and make about 2k a week.I do have a lot of debt, or at least it feels like it to me. the breakdown being;23k in college debt i got getting a bachelors that i never used across 5 loans ranging from 3 to 5% interest rate5k in bank loan debt i got getting my trucker cdl a at 12% interest rate.2.5k in credit card debt from not having an emergency fund and then having emergencies.

One seller was indeed making 90k/year in income however-they will never get a true license. 

Also, for the experienced BRRRR folks out there, are you holding true to the 50% Rule on Cash Flow on each project? 

Is the old adage that landscaping doesn't get any ROI in a middle-class market still true?

In your experience do those rental comps hold true if you go North of Addison (specifically Irving & Kedzie area).

Very true and we were kind of thinking about that 3 year time span as well.