The year that the primary tenants will be in the property will likely provide more than sufficient time for the vacation sector to recover in this area, so that should be a very smooth transition back into that strategyOne thing to note is that whether you're looking at doing a condo or a single family, it's unlikely that either of these will even come close to cash flowing as LTR's, so STR is really your only option for either of these.

My experience is that by choosing a "good" tenant, then treating that tenant really well things go smoothly and everyone is happy in the end.

This transaction was super smooth - my buyers got everything they asked for on inspection, got the property for under asking, and walked away with a cash-flowing asset!

If the property is turnkey, things should be smooth once you get the team acquainted.  

San Antonio handymen ought to know smooth, orange peel, and knockdown.

The way the pieces fit will just not have that 100 year old smoothness. 

Has anyone had experience in what allows this transition to work in a smooth seamless and what makes life more difficult?

Not all of it has been smooth, but it was definitely worth it.  

I protect my clients interest in each deal and contract, make sure it's legal and the process goes smoothly and the way they expect.

In fact 100% of the time the unrepped buyer is the high bid, I counter them even higher for 2 reasons. 1) I know they are still going to go higher when they are unrepresented. 2) So when someone comes bitching that I double ended the deal, Im able to show that I didnt make it smooth sailing for the unrepresented buyer, we in fact negotiated them even higher up in price.