Sure.

HELOC on the TH you're living in sounds the most doable (banks have more appetite to lend when it's owner occupied).Two cents - HELOCs can be great, but it is still debt and you'll want to make sure your base case expected return makes the juice worth the squeeze.

I have succesfully done this on IGMS PMS software.I would also make sure your email is listed on their VRBO account. you will then be able to get inquiries and messages on your email account so you know when someone messages.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

Sister: Wants to make sure her parents are not taken advantage of.

Preaching to the choir I am sure.

I’d recommend interviewing a handful of companies, asking for referrals, and making sure the team you choose has a multi-layer review process—so it's not just one person handling your books, but a team with oversight and checks & balances.And totally agree with @Markus Shobe: you get what you pay for!

Way way too often Mrs. wants to stay, but realistically can't afford to stay with one income....and it is just a downhill disaster finacially the longer they stay.   

Keeping the good relationship with her and thus your grandkids is more important that the rest of it so make sure you are prepared to give and sacrifice money if and when it is required and have certain things agreed up and in writing up front.

Make sure your address falls under that range.