They pick me up, drive around the block, do the exchange and drop me back off hahaha Too complicated bro.

It also appears that there's a STRONG correlation between tax sales and distressed property (plus, arguably, worthless property) - ie it's showing on Zillow it's 400k but for the last 5 years it's been a meth lab with fire damage, or whatever.

I've been reading on the idea where no deposit has to be collected and it insures rent and damages.

An updated roof mitigates potential water damage in the future.

I'm still collecting rent from the tenant, who should also be responsible for any damage as well, right? 

And assume everything is a little worse than it looks given the tenant's stuff is probably blocking some problems and things like the carpet and paint will likely look worse when they move out.Lastly, is it necessary to go over asking?

By nothing I mean no damage to the unit, rent on time, and good communication. 

yes can definitely replace just the bathtub but i would do the surround as well . since its leaking would want to see what the condition is below . very important as water damage can produce mold 

Recently, the mobile phone carriers requires individuals and companies to get registered or all texts will be blocked.

You can't count on believing that the family member will not produce a handwritten lease (real or not), or other paperwork & tactics, to throw a big old wrench in your initial/expected timeline.You CAN expect that if they see you as the big old rich/developer/bad guy enemy, they will do as much damage as they can, and drag their feet as long as possible.See if you can feel out what the relative actually wants/ needs, connect/come prepared with info on resources for local "housing help" options, etc (perhaps), and figure out what you can do to solve the problem (cash for keys with an incentive for quicker move out timeframe?