One other thing to keep in mind is appraisals are estimates not exactitudes.

Your journey is two part - accumulate more wealth, and then how you are going to move it onto your kids - both have substantial tax planning opportunities.Given you mentioned your primary motivation is taxes, a HUGE caveat you should keep in mind is that no matter what real estate investment you make, first and foremost it should make good business sense. 

Keep in mind I will be living here, so each room they work on I have to vacate during the work.  

I'm looking into starting off into real estate investing with my partner and have been looking into the Milwaukee area with a buy and hold strategy in mind. I

One thing to keep in mind is "less is more" when it comes to telling anyone including the Loan officer what you plan to do in terms of living arrangements.

When I read things of this nature, what comes to mind is, did the person writing this actually do that themselves.

WAAY to much work for the money in my mind.. I

I understand thought about equity in properties but what have to keep in mind is how it views from financing side of the table.

One thing to keep in mind is that the tradesperson needs to invest their time and money to do this.

That said, I know on Airbnb that you can edit your payment receipt info and your tax ID info, so the question in my mind is: could you just have the current owner remove all their banking/tax info, give you the password, you go in and change the password and then put in all your bank/tax info?