Quote from @Jay Hinrichs: my advice is to get some cash first.. dont be so focused on super high leverage. do seller finance first .. forget sub too until you are very well established and have ability to cash out the loans or refi on a moments notice @Don Konipol  Don gave you chapter a verse about the sub to risk/rewards.

I am in an R3 zone so I am under the impression I have the ability to do so.

Being clear about what’s covered in the lease and by local laws can avoid misunderstandings and set their realistic expectations.If you do plan to carry out the cosmetic upgrades (because the property is overdue and of course you want to ensure your tenants are enjoying their home to the best of your abilities), try to schedule the repairs at times that minimize disruption.

I know the founders personally, and the ability to call or e-mail when I have an issue and get a quick, personal response makes it worth every penny.

You can do all of those to increase value or sale ability. 

And the ability to adapt is critical: we have seen so many STRs pop up in Milwaukee over the last years, that only the best thrive.Speaking of it: next week at RPA-CON we have a session about STR vs LTR.

Then set up a bill-back for this service.

Now after the fact, he sends us a bill that basically outlines taking care of all the same things the other bit mentioned, but he is  wanting 23K after the fact.  

Doing nothing may be correct for one person, and engaging in a complicated entity structure may also be correct for another person depending on the situation.Each real estate investor/professional has different risk tolerances, different levels of savvy, different abilities in terms of bookkeeping, different estate plans, if one has an estate plan at all, and different relationships.

This could impact their ability to pay rent or want to renew.