Used to see him and his ads all over.

The goal is to minimize unnecessary usage and prevent extra costs, rather than blindly paying whatever bill comes in.

I added a pool and did some landscaping and have been using it as a family winter retreat and renting it to a STR operator the rest of the year.

There are a few markets in the US where you are forced to look outside like LA, SF, NYC, Boston etc, but even for Chicago investors it does not make sense to invest in Milwaukee due to the added cost and complexity

Now, if you were NOT a "real estate professional" you would only be able to:grab the rental income ($100k) and subtract that from the rental expenses/depreciation ($117k), now that extra $17k loss can only be used to offset future rental income, not the W-2 income and dividends and interest income. 

I’ve consulted several different people and they have told me in my situation as an investor expanding their portfolio it makes more sense to keep the extra cash as opposed to paying down rentals.

The quotes were only a few hundred dollars extra annually.

Adding a couple of clean outs on new pipe should be no big deal. 

Adding value to a property and then either selling or refinancing to pull your capital out is a solid way to build momentum, especially if you're okay breaking even on rental income.

Look to see how you can earn extra money while also cutting your spending.