OK,This is a little obtuse but just stay with me.

If so, how do you make yourself comfortable with investing with someone who may not have a lot of experience? 

I currently have an operating AirBnB in Colorado and looking to do a vacation this winter, staying in some AirBnBs while on the trip.  

Be consistent and you will stay there."

That may mean doing something that may make you uncomfortable such as calling them directly if you can get a number or knocking on their door, but you can at least start any discussion with "I live in this property and would like to stay there" so as not to sound like some vulture circling like other investors may appear to them.

Because Saturday and Sunday only amounted to two days, and you would have no business-related activities on these days, the fact that you had to stay until/through Monday to finish the seminar, still means that majority of the time there was spent on deductible activities - thus whole trip, including air and hotel is deductible.

Yes, i researched the title myself and am comfortable that there are no other liens ahead of the lien that foreclosed. 

Try a couple small local banks and big banks and find someone you feel comfortable with and who has the best rate (take into consideration closing costs and other fees, not just APR.)

Long term, I'm looking for cash-flowing properties (buy and hold or repositions in order to build a comfortable portfolio) but I'm pretty new to all the options at present.

I would side strongly with your friends (I believe the technicality on OO isn't being there full time, it's like more than X amount of days for 1 year or something.) so I would say maybe not "move in" but make sure you have some stuff to stay there when you have vacancies.