Quote from @Theodore Sutton: Check out the site meetup.com and also the events page on BP for meetings up in your area to meet people like this and build relationships.

Minimal changes to effect common entrances, no major shifts in load bearing, easy plumbing changes for wherever the new kitchen would be... it's a lot of boxes to check. 

For rental comps, tools like Rentometer, Zillow, and Apartments.com are great for comparing similar properties.Feel free to share a specific property or area, and I’d be happy to help guide you through running rental comps.

I've been checking HOA CC&Rs to make sure they allow short term rentals.

An LLC is not free.

The typical income from a free and clear rental would probably be $800-1500/month - and on a financed rental probably $300/month on a good day in today’s market.  

A good designer and architect are key for a successful project like this and keep in mind these aren't cheap.There's a lot more details to consider, feel free to DM me for more details.

If you're located in WI, check out Premier Point Realty and Homestead Realty....both offer the licensing course at a discount and some of the lowest fees/commission splits in our local market.

Since your homes are free and clear, keep them that way.

Just take what you get for free, which is an Airbnb listing, and just put the best most spectacular pictures you possibly can on there and after you’ve done that, go back and look at your listing and try to think of ways to make those pictures even betterI think that’s pretty much the formula to success in this industry.