I can't comment on whether or not any of that will reverse but I will comment on is that as long as Chicago has the following it will always remain a place for commerce which then supports Real Estate.

Years ago there used to usually be a house right next to a church, called a parsonage, where a minister and his family would live free, supported by the church congregation.

Speak to each type of lender and see how best they can help you with your goals, and do you feel that they will support your investing goals.

Thank you for your continued support 🙏🏻

Dominic,You do not need to wait two years with a fully delegated bank/lender you use the 1st year plus a current profit and loss with bank statements to support deposits reflecting income. 

So either you only allow night charging or you use one of my suggestions with the companies that charge for you or the solar powered systems on a trailer though they probably won’t support more than a couple vehicles.

Overall; check with your bank first for a free option like Zelle, then move onto setting up with a third party player like ZenLordPro (there are numerous rent colleting apps, this one is just pretty easy to use) and you're thinking along the right lines in setting up electronic payments. 

I don't want to involve my husband because while he's supportive, this isn't his interest/business pursuit.

Make an offer with numbers you can support.

Put in a new support wall outside, new roof, fixed walk around porch, new HVAC system, 2 new bathrooms done in the historic style in one and not in the other, new water line,  new floors, fixed wall that was fallen 6 inches from second story to foundation, replaced termite damaged foundation beams, paint and cosmetic stuff, all new plumbing, lots more.