Based on that limited information I would make the repair.

We've investigated condos in the past, but they have multiple limitations, including an average tenant stay of about two years, financing restrictions, and the high HOA fees limit profitability.

I feel like it would limit me from being able to buy the next deal, or find one that we could brrrr, or something.Am I being dumb for struggling with wanting to commit to this deal??

The iron content is at it's limit, and you'll get red stains on anything where water sits as it oxidizes with exposure to air but a water softener will take care of that.

The market rents are carried by the approved section 8 limits which goes up every year. 

Evaluating markets is one thing, but what do you look for in the people you meet in these markets if you can only spend a limited amount of time in person?

All that to be said I don’t think either one is the wrong choice assuming your market doesn’t have capacity limits. 

Lot's of associations have restrictions on rentals which would severely limit your earning potential/ability to rent at all.

My understanding of loans and financing is pretty limited.

The Home possible program from Freddie is one of the programs that was restricted in the past due to income limits but the limits are being revised upwards which will allow more people to utilize freddie's HP to finance a 2-4 unit property with 5% down on conventional.The advantage of HP is that it has lower monthly MI, its conventional financing so not as restrictive as FHA (which can also work for 2-4 units with 3.5% down payment), HP does not require you to meet the FHA SS rule (required on 3-4 unit FHA financed properties).I've seen freddie's income limits go up about 10-20% this year for 2021 so that might allow more people who are looking to "house hack," to utilize this program.HP only allows max 2 financed or owned properties total so its a perfect for someone starting out to house hack.