No penalty and no tax- look up ordering rules for Roth IRA distributions in irs pub 590 and irs form 8606.Roth “Contributions” can be removed at any time without penalty or tax.  

Then anticipate that the property is being sold remove problem tenants.   

Otherwise he wouldn't be part of my company.Again I am removing myself from this so you deal with him directly i.e.

No idea what's going on in that town, maybe it's really good drugs or something, IIRC a casual google search did reveal it was near one of the big annual music festivals where 20somethings go to remove their clothing, dance, and imbibe various substances. 

For now, just follow the first sentence in this paragraph.Also, you should have some sort of signed agreement that if he vacated the property for more than say 2 weeks and rent is not paid that you can remove his stuff and...whatever...call a friend he identifies to get it, place it in a storage unit and mail him or a friend the combination. 

My main goal is to make most of it Automated and just hire house cleaners, snow removal, and have a handy man at the ready!

That would leave me responsible for snow removal and lawn care as well as waste removal (which would be around $93 a month for a 4 cubic yard dumpster which should be sufficient.First Analysis - I wanted to get a ballpark figure of what expenses would be for the property if it hadn't been recently renovated, so I ran the numbers assuming higher expenses for repairs.

She has to remove the $40,000 from her IRA and declare it as income.

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You don't have any mention of landscaping or snow removal.