As @Steven Hamilton II points out - if you got insurance money, it was reimbursed - and therefore can't be claimed as a casualty loss deduction.If your casualty happened in a federally declared disaster area you can apply the casualty loss to the previous year's tax return (by filing an amended return) and it might get some money in your hands sooner. https://www.irs.gov/pub/irs-pdf/p547.pdfThe situation is continuing to unfold, so unless you were desperate, I'd wait.

We added recess lighting, got the laundry inside the house, converted the extra room into a gym and also painted the whole house including the tiles in the bathroom (since me and my girlfriend were experts in painting from all the experience we had from the back house).All of this costed about $30k.

I wish I was able to invest there sooner.

They know seniors are on fixed income so the rent price tend to be cheaper and if not, most times the amenities like gym, laundry, electricity or gas are already included in the rent. 

The sooner you want to retire the more cash flow you'll need in the present, so a 30yr would work better.

Additionally, I'd increase your Vacancy to 8% so that you are saving up aproximately one month of rent per year (1/12 = 8.333%) and I'd defintily increase your CapX to 10% as CapX is for major repairs and since this property was built in 1984 I'm assuming it will have some maintenance needs sooner rather than later.

I probably could have made more money if I held it longer but circumstances changed and I wanted to sell sooner.

As far the contract goes I’d try to get as much time as possible, 45 days if you can, with an option for you to close sooner in case you find your buyer and they can close quickly.

He could be the nicest person on the planet at times (otherwise I'd of been done much sooner).

Must make financial sense in order to take on debt, no speculation.Find a house hack, live and flip sooner than later, continue to live out of the camper until that happens.60% or greater savings rate indefinitely.Over the next 3-6 years, keep one of my full time jobs, be per diem at least one more and dollar cost average real estate to a total of $5,000 after expenses income.