I presume a stagnant market, with only necessary sales (death, divorce, downsizing, and relocations). 

If you transfer it now, you lose the sec121 exclusion if they should ever have to sell in there lifetime, and more importantly you/they lose the stepup in basis upon death. 

If both of your names are on title, then both of you should have to sign to remove one (or have a death certificate). 

For example if one of your unlicensed carpenters falls off the balcony and get's hurt or worse, you're paying their hospital bills, or could be on the wrong end of a wrongful death suit in a worst-case scenario.

These transaction costs kill the margins and you realize the death by a thousand paper cut disposition approach isn’t worth the effort and ultimately sell as a package to another investor discounted and you never see the equity translate to an actual gain.

I would like to buy my first rental property in the next few months in the Milwaukee area using the brrrr method, but I am scared to death to make mistakes and lose the money that I worked so hard to save. 

That is why you can get 500k in death benefit for less than $20/month in a term policy.

(Title IX As Amended) [42 U.S.C. 3631] Violations; bodily injury; death; penaltiesWhoever, whether or not acting under color of law, by force or threat of force willfully injures, intimidates or interferes with, or attempts to injure, intimidate or interfere with--(a) any person because of his race, color, religion, sex, handicap (as such term is defined in section 802 of this Act), familial status (as such term is defined in section 802 of this Act), or national origin and because he is or has been selling, purchasing, renting, financing occupying, or contracting or negotiating for the sale, purchase, rental, financing or occupation of any dwelling, or applying for or participating in any service, organization, or facility relating to the business of selling or renting dwellings; or(b) any person because he is or has been, or in order to intimidate such person or any other person or any class of persons from--(1) participating, without discrimination on account of race, color, religion, sex, handicap (as such term is defined in section 802 of this Act), familial status (as such term is defined in section 802 of this Act), or national origin, in any of the activities, services, organizations or facilities described in subsection(a) of this section; or(2) affording another person or class of persons opportunity or protection so to participate; or(c) any citizen because he is or has been, or in order to discourage such citizen or any other citizen from lawfully aiding or encouraging other persons to participate, without discrimination on account of race, color, religion, sex, handicap (as such term is defined in section 802 of this Act), familial status (as such term is defined in section 802 of this Act), or national origin, in any of the activities, services, organizations or facilities described in subsection (a) of this section, or participating lawfully in speech or peaceful assembly opposing any denial of the opportunity to so participate--shall be fined not more than $1,000, or imprisoned not more than one year, or both; and if bodily injury results shall be fined not more than $10,000, or imprisoned not more than ten years, or both; and if death results shall be subject to imprisonment for any term of years or for life.TITLE 28, UNITED STATES CODE, AS AMENDEDSection 2341.

I would be scared to death to invest out of state again, for my whole life if that happened to me. 

Hot Spot no pun intended its probably the hottest spot in the US thats not in death valley LOL