Landscaping upgrades, exterior painting, new siding, a new roof, and upgraded front doors and windows can dramatically increase ARV by improving the home's exterior appearance.5.

While it's positive after expenses and has potential for improvement in year two, it’s been a bigger hassle than anticipated and taking attention from other priorities and areas of our life with not enough return. 

So far mostly people are telling me I'm probably stuck until their lease is over. meanwhile I also need to pay down my debt and improve credit score. 

There are of course exceptions, but so long as you pay your taxes, the US government won't challenge you or your business, so long as it's legal and it complies with the United States law.So the immediate answer is yes, you can do.

--reach out and thank them upon getting the booking and ask if they have any questions--send a "Welcome" email or automated message during the week prior to arrival--reach out the day after arrival to ask how everything was the first night and ask if there is anything that the property needs--reach out at the end of the stay (that morning or within 24 hours) and ask how everything was, anything to improve, anything to add to the house and then offer an incentive for returning guests.My 2 cents,Mike Absolutely stay in your place as Mike said.You will see things the cleaners will never let you know about.We stayed in our PF will putting up the Christmas decorations and found a cracked plastic shelf in the fridge. 

This would improve the property value and also allow you to lease out the 5th unit.

What are the biggest challenges people have faced with this.

That process has direct lender involvement.Where the challenge lies, is when unsophisticated "investors" with no experience, no money and no reserves use creative financing (often called wrap, subto, lease option, seller financing, land contract) to purchase properties and along the way there is a "hiccup".

The more challenging stipulation is you would need to use it more than 50% of the time for business use (and you need to log the miles to document that).  

Being young will present challenges in a field where experience is highly valued not just with lenders.