for me  a handful since early 80s  now in those days I was ONLY buying land that had owner contracts on them. 

I would sell it and use that money to either buy a rental property or invest elsewhere.

I’m weighing two options for our housing situation and would greatly appreciate your advice, given the complexities involved.1.Renovate and Buy Another Property•Invest to renovate our current home adding a bedroom to the house given our family outgrew the house.

-are you buying with conventional or DSCR financing? 

Great for someone looking to buy their first investment property. 

My strategy is buy-and-hold, not buy-and-sell.

Yes, they will do many things better than you, but some things it's not possible for them to be as attentive and quick responding as you.Also, no one's perfect, so keep tabs on them in general.Regarding holding or selling: why did you buy this in the first place?

Fatal mistake to buy that on the forward curve.My recommendation would be to get out of this position; the STR is in an extremely oversaturated market and the underlying asset is a clone of many.

@Joshua ParsonsI've been dipping my toes into the whole "buy a house for $1" thing that Italy is doing.

One thing you don't want to do is to buy based on proforma and have a negative cash flow property, especially on your first deal.