This can be very subjective, so you will have to evaluate what you truly value and whenever you spend money (whether it be $100 or $1,000,000) that it has some true, impactful purpose behind it.People also aren't methodical when it comes to saving money.

The 3 most important factors on a macro level in evaluating a market in my opinion are 1.

To both your comments Huong Luu and Hai Loc: as I'm going about this from a top-down approach, how would you evaluate all the individual listings out there and understand whether the market has undervalued units or not?

Chicago has several outer-lying suburbs to consider buy & hold strategies while your neighboring states in the midwest, like Indianapolis, have great economies to support all kinds of real estate investing.Out-of-state investing requires a lot of research to start and, as mentioned above, a lot of networking to vet the team you'll need to work with to move your project forward.Start by getting connected to a realtor who will have access to run comps for you so you can correctly evaluate potential ARV so you know what you'll need to put into your BRRRR property to maximize your ROI.

You are welcome to ride along as I evaluate the properties. 

If you figure out how to make the bids, and do the due dilligence to evaluate the homes, get all utilities inspected prior to closing etc.. then you are doing the work most people won't and you're more likely to get a deal here.

Watch Brandon's videos on how to evaluate a property and then practice it daily.

Agents can help you evaluate deals on the MLS and ideally bring you deals not yet posted there. 

Evaluate your home every year and update things as needed.

If you were slow in getting the lender what he needed in order to complete his evaluation, then consider that it may be your fault.