Also have easements for fire truck turn around.

Costs will always go over budget. 

Site cleaning may be the single most underfunded line item on construction budgets which often leads to dangerous work sites.

I'd also recommend joining a local Indianapolis based REIA asap. the REIA will provide a group of investors who could get you some contractor recommends if you decide to GC the prop yourself.You said it "needs a little work done" but budgeted $50k so those two things kind of contradict unless the home is a larger home...just curious, what's "a little work", if you haven't had an inspection yet and don't feel comfortable evaluating the costs on your own?

Should I focus on teaching him the basics of personal finance, like saving and budgeting, or is there a way to introduce him to more advanced concepts like market analysis? 

Hey Chris, If your agent is only using RCM, they might not be familiar with platforms like Costar or LoopNet (which honestly should not be the case), or they simply may not have the budget to cover the upfront listing fees, which can get pricey.I’d circle back with them, address the plausible elephant in the room, and try to figure out a game plan to get your property on these other platforms.

Even without a budget for repairs/etc - let's just define "cashflow" as income left over after PITI & utilities for a moment - Mac Groveland and Highland Park are going to be tough.

Start small with a property within your budget and skill set, using HELOC for funding.

You should budget around 2-5% of the purchase price for closing costs.

I think you would need to ultimately know what your goals are and honestly what your budget is.