My buildium software makes it easy for me to charge water bills so I don't need a billing company.I did not want to use a submetering company with provided equipment that charges a each tenant a surcharge depending on the level of service that they provide.

I did once a week on Saturday's for 11 weeks and it went fast and trust me you want to go once a week for studying and preparing yourself.

The amount may change, Zillow is often within a considerable level of error  The bank is going to loan you a percentage of that value. 

Would it be good to make it as a living trust or under corporation to have enough for expenses and distribute rental income?

I've seen other posts that suggest conducting an ARV analysis to get this answer, but I just don't have enough experience (or confidence) to trust the results that I would achieve.

Assuming Illinois doesn't have state-specific forms that are different, look at paragraph 6 of the deed of trust that any owner occupant who got any 30YF Agency loan signed at any closing table within the last 5 years. 

I don't know how much I trust him personally, but he did make some good points, one of which was using SFR as an Assisted Living Rental.

If they have no stance against it, go for it; you'll be able to provide a high level of service to that place being just up the road.

Make sure intentions are clear on both sides and you'll avoid this situation where both parties assume something different entirely.1025 seems like it's almost roommate level rent for DC and your friend is getting a decent deal but more important is comfortable w/ the spot for another year.... if you try to get too aggressive against the landlord they'll look to evict.

If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.