If they stayed later, the cleaners would naturally show up while they're here and they'd have the awkward interaction haha.

Meaning, no taxable gift at all if under $15k in interest for the year.More steps and paperwork involved to adequately record as a loan and not a gift.

I hope I've been able to describe this adequately.  

I think our natural inclination to get more cautious as we age coupled with the perception that the real estate we can touch is somehow more secure. 

There is very little natural light and I am wondering if that will put off tenants or potential buyers when I sell?

Also be sure to account for snow removal and things of that nature if you’re buying multifamily

Are there any particular guidelines that need to be followed, and are there any pre-written packets, or something of that nature, that I can present to a potential investor, and any "canned" type presentations that can be tweaked for each potential project?

You also need to know that condo reserves are adequate, whether there's any pending litigation and pending special assessments.Consider an escalation clause for your offer. 

Most of the work that needs doing is cosmetic in nature.

Naturally I’ll consult an attorney before moving ahead but curious if any of you have had this experience.Appreciate everyone’s replies.