Last thing to look at (and right out of the pages of our client's own experiences) might be starting a transition of wealth in the form of using 1031 strategically to purchase property that your heirs live in until you pass and they inherit. 

HiI am real estate investor and Realtor living in Naperville, IL.

Use STR-specific insurance to protect both parties and automate operations with platforms like Airbnb, TurnoverBnB, and PriceLabs.Taxable income from the STR must be reported, but you can deduct related expenses like cleaning, utilities, and furnishings.

I informed them that their contract states they are expected to pay up until the end of the agreement regardless of living their or not. 

.* Receipts and Expenses: Once I brought to Jenny's attention that we were 20k above budget, she refused for days to give me the receipts, saying that I needed to give her my credit card statement first.

It is actually better to start with a slower season and welcome expensive guests when you know what you are doing. 

Hiring a lawyer sounds expensive, but it is way cheaper than hiring a amateur (in this case yourself) who costs you money and provides no results (and then you need to hire a professional anyway).My personal philosophy is to "do it right, or do it twice" and its way cheaper to do it right once. 

They are more expensive than conventional, but not by a huge amount.

We are seeing people move from higher cost of living areas like Raleigh, Durham, chapel hill, and even Greensboro.   

.- **House Hacking:** This can be a great way to start, especially if you're looking to live in one of the units.