Blending personal seasonal use with income-producing strategy can work beautifully — but only if it’s structured correctly from the start.

$200,000 in the Midwest buys you a 100+ year old property that is held together by duct tape and will need a lot more in capex over the next 10 years than the cashflow it produces; aka a money pit. 

The only side note on this is if you can redeploy your capital after all expenses into a better producing asset then selling makes sense.  

Filing to court date times have actually gotten faster in the last few years so that can’t be what you mean.

Been considering getting into learning to how to file taxes for Airbnbs.

A complete collateral file and verified pay history can significantly impact how confidently a buyer prices the asset.Pricing is heavily influenced by true LTV rather than optimistic valuations.

If you lived in a property for 19 years, moved out and turned the property into a rental, you should be able to exclude up to $250,000 or $500,000 of capital gain depending on your filing status.The only gain that wouldn't be eligible for exclusion is the depreciation taken on the property that it was a rental for 1.5 years.Best of luck!

A $10,000 loss would produce the same tax savings either way.

You don’t amend prior returns — instead, you file Form 3115 (change in accounting method) and take a one-time §481(a) catch-up adjustment in the current year.

Here the IRS has a reason to challenge your credibility and the credibility of your self-produced numbers.