For estimating rehab costs, try using the BiggerPockets Rehab Estimator Tool or get quotes from contractors through sites like HomeAdvisor or Thumbtack.

We are listed on about 6 sites and besides the typical Airbnb and VRBO, we've had success with Travelstayion as well. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Please share your information with me directly.

Thank you Tom and Dawn for sharing your experiences with Solera too.  

It’s done but can be risky.Just my 2 cents and how I approached my real estate / home ownership process - not saying it’s right or wrong just sharing my experience

Development projects can vary from a 1-lot Single Family home to 20-acre subdivision, to a 4-acre commercial site, etc. 

You can also use sites like rentometer to help confirm your rent price.

Thank you for sharing your findings.

Can anyone share their experiences or advice on how to make this process smoother?