Since I am retired and have been able to par my normal taxable annual income down to a bare minimum it might be possible to use a small portion of the capital gains in future tax years at Zero tax rate or at least at a very desirable low rate.

I normally get rid of squatters in 24 hours. 

You are looking to see if they are maintaining the home like a normal person or if they are abusing or neglecting the rental.

The truck you bought will instantly lose value the moment you drive it off the lot, it will depreciate over the years due to the miles you rack up on it and the normal wear and tear of a vehicle.

Does this sound like a normal timeline for closing in NYS?

Buy the house as you normally would, then once it is yours, draw up a lease agreement for whoever you are renting it to-even if it is family that you are renting to.

If there is a potential for loss of any kind, then you are using their funds for your benefit - i.e. gambling with other peoples money - so definitely a place you don't want to go.

If this property had been in one of the areas zone for more density they would surely have done a normal "Seattle six-pack" of 0-lot-line townhouses but instead they short platted 2 lots to still in effect end up with a six-pack even though in an area not zoned for it, at the cost of having to sell units as condos and deal with other ADU limitations (e.g. 1000sf limit).In 2023 the State mandated Seattle-style ADU regulations across all urban growth area cities/counties, going even a bit further (2 of any combination of attached/detached allowed).

I've done everything in residential real estate (wholesale, rehab, normal rentals, short-term vacation rentals, turnkey, property management, private lending). 

An assumed VA loan would plug in place of the new property purchased in this example.Also, you have a one-time option to have your VA loan eligibility restored regardless of how much you have used; normally you have to dispose of the property, meaning sell or pay-off to have it fully restored.