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The initial investment is already invested. This ain't no buy to let situation and I don't define money I never had as a 'risk'. Selling my flat and having the new place I buy collapse into a pile of dust is a risk. Not earning money off something, not much of a risk.
Stamp duty - is it higher if you already own one property?
I would be living in the second property, yes.
I have very little appetite for 'investing' in that sense. I'd rather pull out my pubes one by one than follow stock markets. Then again, if tenants trash my flat I'd be spending my spare time concocting more and more elaborate revenge schemes. So, that could be a time suck...
It depends what you define as risk. As you say there's the lost earnings, £300k or whatever invested elsewhere could earn a decent amount.
There's the costs of the property upkeep and bills. There's also the increased stamp duty on a second property which could be hefty.
If you want a second property as an option to live in or whatever then it's worth keeping.
If you want it to make money then you're probably better selling it and putting the money elsewhere.