In my opinion, from appraising hundreds of homes with PV systems, they may add a "bonus" factor (additional appeal, etc), but that may not translate to a significant increase in price, and not worth the price to install them. 

Different types mailers will appeal to differ types of sellers at different stages of their situation.

It does have Window A/C, the floors creak, and the basement is kinda dank, but it's got the most curb appeal of any house on the street and a lot of the cap ex stuff has been done. 

And while the amazing architecture of ONE, OSE, and Kenwood has a lasting appeal, I do worry about rents and vacancies once all of the cranes come down and inventory geometrically increases near downtown.A 1031 exchange would let you and your brother separate. 

.) - I would approach the one you think would be the most amenable to having their mailing address used as a local contact.Alternatively, if you live close enough to the property where you fulfill these roles, I would appeal to the appropriate authorities with your situation, and explain to them that you understand the intent of that restriction, and that you fully intend to bear that responsibility even though your address is on the other side of a line some dude drew on a map many decades ago.A final "hail mary" might be that you set up a "Mailboxes Etc." post box or something similar. 

Old Homes Pros: Tend to be in better locations closer to amenities and main attractions, more likely to be walkable, often have larger lots, houses and surrounding area have more "character", sometimes they have features like old growth wood and other elements that add value and longevity, no HOAs; Cons: Near endless potential for expensive issues of every type because of the impacts of time, neglect and old building materials and methods, require more work and money to make them modern and appealing, can be tricky to financeNew Homes Pros: Far less maintenance and potential for issues and may still be under the builder warranty if issues do come up, modern design elements and fixtures, often in good well-funded school districts; Cons: Homes and neighbrorhoods have a manufactured feel and less character, lots tend to be smaller because developers want to pack in as many units as possible (especially in high $$$ markets), tend to not be walkable because the areas adjacent to the best attractions/amenities have been built on already, sometimes built with low end materials, HOAs restricting what you are allowed to do to your property 

You'll see the differences in rent among those neighborhoods.Since you're looking for A/B class neighborhoods I suggest focusing on the NW Chicago areas I mentioned and perhaps consider other north side neighborhoods but the cash flow won't be as appealing due to the higher prices and taxes.Agreed with @Henry Lazerow on Elgin/Aurora if you're looking for very affordable 4-units (<$500k) although I would not describe those areas A or B class but if you screen well you'll be fine.

For instance, a bedroom that is at the end of a hallway, and which doesn't share walls with any other bedrooms or common areas provides a lot more privacy than a room that shares a wall with a common bathroom, a second wall with another bedroom, and a third wall with a common area...a house that has 3 stories with only 1 bedroom on each story might provide more privacy than a house where all 3 bedrooms are on the same floor ....extra privacy usually results in less likelihood of disputes between housemates about issues like noise, messiness, etc....If you plan to rehab the property, sometimes, it's possible to re-configure the floorplan of a house in ways that create more privacy for each bedroom, add bathrooms, add separate entrances, and generally make the property more appealing for rent-by-the-room tenants.

When a tenant calls to contest charges, I allow them to speak their peace, then I tell them I will send them instructions for filing an appeal.

If the margin is too similar to a long term rental, then I'd personally pass and find a more appealing market.