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. 

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

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.

And don't even get me started on utilities.

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

Hi Chase,I'd recommend leveraging your experience with a lender and utilizing seller financing options.

You should utilize resources like BiggerPockets, build a team, and use online platforms to find potential properties.

You can then find a multi unit that at least has one vacant unit so you can utilize your VA loan.

You have to audit all of their accounting because inevitably late fees will change every statement, utilities are sometimes billed back (or not at all), and god speed if you have a delinquent tenant.