With 12 properties I don’t want 144 $40-$50 checks (or even that many electronic drafts) that I then have to allocate to the correct property’s Expenses, per year. there might be a $5/mo savings for paying annually but I’d do it even if there wasn’t. 

As others have said, the correct answer is: It depends!

You're correct - some of the suburbs do carry a heavy property tax burden for sure. 

The thing is though, you don’t know when the correction will begin.  

Though one minor detail is that "1099 employee" is probably not the correct terminology - one is usually either an employee (W-2) or a 1099 independent contractor.

Great question, it is very important to gather all the correct information and documents from the seller if you are taking over tenants.

By observing your business, I can confirm or correct my plans and systems.

However used correctly the buyer is not leaving a ton of money on the table and pays the most over any other buyer.. as their price beats the next highest and best by a set amount of money. if other offers are higher without and escalation then they will win the deal.. 

You just need to execute it correctly and work out the terms.

RyanThere's absolutely no guarantee that the lender who said your DTI was 52% knows how to calculate rental income correctly.