Also, there's the added risk of being compliant with federal regulations & state laws as well as properly assessing/vetting both the borrower and the property.

Don't think it's worth it for 1 property.Vrbo and Airbnb will sync calendars with each other and send basic messages already.Vrbo has free built in pricing tool.

Start by learning basic metrics like cash-on-cash return and cap rate, and check out resources that dive into rental market analysis.

My basic philosophy is that if you can't handle the little things, then you can't handle the big things.

He was basically Someone that was in their early 20s maybe a relative to someone in the coaching company.

Another thought you could just keep the tri-plex and gift them the net income each year...it's basically the same thing without any transferring. 

For example - you're starting a $100,000 remodel on a propoerty that you have acquired, the Scope Of Work includes basic lipstick stuff like a kitchen remodel, a bath remodel, and new flooring and paint.I would start with a draw of no more than $10k, that is more than enough to get anyone going and it shows your good faith.

Basically, what you'd be doing is reaching out to a lender and letting them know "I'm planning to buy 123 Main Street in 3 days with cash.

I have heard it’s cooled down quite a bit and assessing if it’s still a worthwhile option to consider as a market for str or even mtr? 

Do I consider it as an SFH and assess potential rental income based on SFH?