In reality he is a high paid, likely already working a ton, attorney - he very well may not want to average an extra 10 hours a week of work year round to make it work. 

@Lucas DeAndradeWith the investors I work with they are  normally acquiring and average of 4 properties. 

Recapture typically happens only when you sell the property.If you use the property partly for personal use and partly as a rental in a given year, depreciation and other expenses must be prorated based on the number of days it was rented versus personal useBased on the current tax laws and regulations, once you've taken bonus depreciation on an asset, you cannot "capture" additional bonus depreciation on that same asset in future years, even if the rates increase.In the 2024 tax year, the rate for bonus depreciation is 60%.

What I usually see is that they start with the average $/sq.ft of the sales price in the area.

In order to avoid questions from the tenants, I was upfront and told them that the current furnace is expensive to run because it is inadequately sized for the house (I didn't mention details about lack of a heat pump) and we made the decision to change it out for a gas one ASAP, which will go to their benefit, and all we need from them is to add gas service.

Just be sure to factor in interest rates and fees when running your numbers.Know Your Numbers – Accurately estimate rehab costs, holding costs, and selling expenses.

It costs roughly $100/mo but is well worth the expense.  

Especially in Milwaukee.And I would argue that average appreciation over long periods of time, have not much to do with hope.

You could house hack by purchasing a small multifamily with an FHA or conventional loan, reducing your living expenses while building equity.

I dont know the terms of this specific home equity agreement but the ones I have seen in the past were pretty expensive.