What type of asset is in short supply? 

The penalty and tax will remain, but there may be other offsetting tax benefits in other areas that will help lower your overall tax bill.Your expenses to fix up the house can either be an immediate expense or a depreciating asset, depending on the facts and circumstances surrounding your "in use" date. 

(Somewhat) Hypothetical scenario,An elderly owner with 2 children owns an asset outright and has owned it for 60 years.

It is a very serious mistake to allow personal feelings to dictate your business practices however in your present situation you are clearly preferring to operating as a hobby investor.

Seller owes 300k on the property and would prefer an all cash deal if it lets him walk away with 150k.

Seller owes 300k on the property and would prefer an all cash deal if it lets him walk away with 150k.

Depending on your budget, drive-able might be best but it also depends on your preference.

I had a Gallardo previously and I prefer the size/agility of the Huracan over the Aventador.

I would suggest that you sell your liability as soon as you can, yes I said  liability, It is called an asset to brainwash you to think it is but when you add the property tax and maintenance, you'll see what I mean.

@Dave Atwal it sounds like you've done all of the right things to protect your assets.