If you do so the income from that asset now becomes taxable income, whereas any income generated by the asset inside of Roth 401k can be pulled out as distribution tax-free. 

Do you try to pay based on what you think the value the property is generating, prior to potentially gaining the upside?

So many of the variables in your analysis would be people and their opinions on value and where the market is going.As you mention, after tax cost is a concern as your rentals may be generating taxable income however your rent is not tax deductible. 

If you meet people that are operating illegally and KNOW it, they generally hide in the shadows, avoid giving out much info on themselves, and are kind of like cockroaches that scurry from the light.

That is the wrong way to operate.

I totally agree with you, Anthony, and it makes much more sense to me now after reading your response, so thanks again for sharing.Another long-term goal of mine is to own and operate a vacation rental in Orlando/Kissimmee.

My team and I are working on the operating agreement presently with a goal of having a plan in place by the start of 2018.

I'm here to learn how to leverage that to generate more wealth and income for our family.

The sale generated the recognition of gain. 

I am reviewing a property management agreement and came across this clause RE: Indemnification that seems too broad:INDEMNIFICATION:(a) The Owner shall indemnify, defend and save Agent harmless from all suits and/or other legal proceedings whatsoever and cost incurred therefrom in connection with the management of the Property and from liability for injuries suffered by any employee or other person whomsoever, except in cases of willful misconduct or gross negligence on the part of Agent or its employees, (b) The Owner shall indemnify and hold harmless the Agent from and against any costs, loss, expense or damage (including attorney's fees) suffered or incurred by the Agent arising out of or related to the enforcement of this Agreement arising out of a default or other breach by the Owner, the management, operation, improvement, alteration and leasing of the Property, including all other activities arising out of or related to Agent's duties under this Agreement or as a result of any act or thing done or permitted by the Agent or its agents or employees; provided, however, that such indemnification shall not apply to any such cost, loss, expense or damage to the extent that the same relates to or as a result of conduct by Agent which constitutes willful and wanton misconduct.It seems like if one of the Property Manager workers (aka Agent) slips and hurts himself while cleaning the floor the "Owner" is then responsible.