Transparency, daily & weekly updates and follow-up with all concerned parties.

Regarding BRRRing OOS - it can be very dangerous:(Too many newbies take contractors and agents at their word, when "trust, but verify" is extremely important.Given you're in Chicago, would recommend you plan 2 trips for a BRRRR:1) Initial walk-thru with contractor(s), which you should video for documentation & accountability.2) Final walk-thru BEFORE paying out final amounts to contractor(s). 

Or ferry which runs daily.

So, I am asking for some advice on how to prepare a pricing and marketing plan to try and rent it as soon after closing as I can.

From real estate investors to other small businesses, I talk to people daily who have no idea about the potential liability under the Telephone Consumer Protection Act ("TCPA")(47 U.S.C. 227 et seq.).There are two initial issues that can create huge problems with your suggestion.

I have a 401k, IRA, and pension in place to help me achieve retirement quicker, however I definitely feel the squeeze on a daily basis and always feel like I'm living paycheck to paycheck.

It changes daily. 

I wish I would have had more knowledge back then as that is a growing resort that gets a lot of weekend and daily traffic.

if she had contacted me, I would have shown her what was planned to finish and discussed the financials. 

I do my best to stay on top of the renting laws as an agent who works with investors on a daily basis.