I purchased my condominium in California about 10 years ago. I initially lived in the property but moved to a different city for a job so I've been using this place as an investment property for the past 5+ years.

For the last couple of years, I've lost some tenants due to some issues with the building. I've been managing this property remotely and it's been very stressful; therefore, I made a decision to sell my place.

I currently don't have any tenants and not planning to have any until I sell the place. I still have a mortgage to pay for so I'm bleeding money out the door every month.

Ideally I would like to sell the place and do a 1031 exchange and purchase another home closer to where I currently live; however, due to COVID's situation, inventory around my area is very limited.

If I were to sell the place outright and not do a 1031 exchange, I would be losing out on close to $100k in taxes (w/ my income and capital gains).

Here are some of the options that I thought over:

Paying Taxes-- Sell the house now and try to do a 1031 exchange but due to limited inventory, I'll most likely won't find a place to buy in time and have to pay $100k in taxes.

Pros: Better chance of selling since the inventory is low in the area. Can hold onto the money until the pricing will lower in the next 1-2 years. Don't need to rush to buy a house in 45 days. Won't have the place vacant for too long.

Cons: Will lose out on $100k in taxes

2) 1031 Exchange-- Holding onto the condo until there's more inventory in the market (vacant for ~1 year. *Assuming prices will lower due to recession) and pricing to go down

Pros: Will not have to pay $100k in taxes. Pricing will go down due to recession

Cons: Will leave the place empty for about a year. Need to do a 1031 exchange so I'll be rushing to buy a house. Decrease in property value and may not be able to sell the house at all. My condo's pricing will decrease

By doing simple math and writing down the pros and cons, the obvious risk adverse option is (1). But losing out on $100k on taxes sounds silly and many investment related books that I read always suggest deferring taxes or finding a work around.

Thank you for reading and would love to hear your honest feedback and advice.

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