John Underwood look at it this way, did you sign a contract with Homeaway to exclusively list on their site in return for a premiere listing?

with no history of investing, you best option will be to purchase a property as owner occupant and house hack. this is the main way people make purchases under 20%. in fact, most banks want 25% for investment property. you will find that any loans under 20% are going to be almost exclusively for owner occupied properties

Also, if you have more than one credit card (MC/VISA), use one exclusively for rental, will help keep track of expenses. 

@Lauren KeenTax Strategies for the Savvy Real Estate Investor is good book and does make the investor think about deductions he/she is entitled to.You are entitled to a home office deduction if you had an area in your home that you used for your business(file cabinet to save tenant files, office desk to take and place calls) that was regularly and exclusively used for your business.There is one caveat with the home office deduction. 

I'm also local to Chicago and own multifamily exclusively in the suburbs.

Would a setup where a historic building with 7 rooms, 2 bathrooms and a kitchen is rented out by the room exclusively to air force personnel, potentially furnished? 

Just have a little question about sale tax exclusion.

We are just starting out in real estate and are looking to mainly set up passive income, but not exclusively.  

I like the cloud based option better and we use Mac exclusively so rent manager seems out unless it is absolutely the "way to go".  

Our insurance went to $1600 p.a. but we added it back into the rent but we had to accept exclusions for painting & any other flammable storage.