Most likely relying just on real estate income at the beginning will not be a good idea.

You want the insurer to be locked in to defend anyone who is operating that rental if they're named individually for something they did or did not do while operating it Thats a very smart idea!

I have no idea how much it would cost to pull carpet out, install flooring or any remodeling.

I've been playing with the idea of becoming one in the hopes that it would help me branch out and meet more people, learn the lingo and just be more involved overall. 

Is it a good idea to start skip tracing or returning to an area on my day off and door knock or leave door hangers?

sure. but this idea of cash flowing in month 1 or year 1 is extraordinarily unlikely in today's market.

Hey All, We have been searching for a place in DC proper for a house hack.

Sorry for the questions just trying to get an idea of what some expectations are.

STRs require a lot more cash up front so you just want to make sure you have a good idea of what you're getting into first :) I own STRs and love it but I also wish I had learned a little more about the analysis and management prior to going live - I did some of that on the back end and could have been successful faster.Another idea is to talk with some owners 1:1 to see what advice they would have for someone starting out.

I am happy to shoot you a PM with some Chicago insurance referrals...I also know @Jason Bolt here in BP is active in that space.I think the better question besides cost is are you properly protected.