@Christopher SarmientoHow was the 50k estimated tax calculated?  

While researching my options to reduce my 2024 tax burden (already maxed the 401k and HSA), I see that it is possible to buy an investment property, use it for Short Term Rentals and as long as certain conditions are met, I can accelerate the depreciation which can be used as an offset to W-2 income.

The life estate will spell out the obligations of the step-father (taxes, utilities, insurance, upkeep - or even a base rent that you could use to cover those costs).

What I have done in this situation is I acquired the property and then had the individual sign a long term renewable lease and the cost was $1/yr + the costs of insurance and taxes. 

Many tax sale properties derive from estates where the heirs take no action and the property goes to tax auction.

Is it maybe because this income hasn't been captured in a full year's taxes yet?

Obviously, all this income will funnel down to you on your tax return, but you should have go into your LLC if you have it titled that way

At the moment Im into wholesale and tax lien/deed.

You could use the equity in your house, likely tax-free since you lived there the last three years.

I think you're right if you categorize them on your taxes as maintenance they will limit you more on a refi. 2.