I can estimate most of the cost, taxes, insurance, utilities, PM fees, and such and I know that should be provided in the expenses but when it comes to the actual maintenance of the property, what strategy do you normally use?

Hi, we have a second home in Oregon that we only utilize every other weekend. 

I would go back to that company as you are doing and reconcile this, bring plans, drawings, the license number and permit number with you to make sure you show you are doing it all within the city regs too so they can get you back online. 

I am already searching on line for more information on neighborhood classes in my area.

Primary house purchased cash $965000Spent $75,000 updating/remodelingOther holding expenses to date: $12,600 (annual taxes and utilities for two years)Home now appraised at $1,325,000.00 We are considering selling our primary house, finding another primary that we can live and flip again over two years.

Has anyone utilized this strategy for a longer term and have any feedback? 

Our properties are a strong mix of appreciation, rent growth and cashflow positive in year 1.Going on 6 years I have never had to even give any late notices, etc. for my northside chicago rentals, it's multiple applicants 700+ scores when list the units online. 

You would then do the math to remove that exemption and see what the resulting yearly tax amount would be.Since it's your first time being a landlord, it might make sense to utilize a property management company or agent to find and screen a good tenant.

And don't even get me started on utilities.

Are they separately metered for utilities, or can you bill back to residents?